3-(3-aryloxyphenyl)-1-(substituted methyl)-S-triazine-2,4,6-oxo or thiotrione herbicidal agents

ABSTRACT

There is provided a 3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo or thiotrione compound having the structural formula I ##STR1## Further provided are a composition and a method comprising that compound for the control of undesirable plant species.

BACKGROUND OF THE INVENTION

Weeds cause tremendous global economic losses by reducing crop yieldsand lowering crop quality. In the United States alone, agronomic cropsmust compete with hundreds of weed species.

In spite of the commercial herbicides available today, damage to cropscaused by weeds still occurs. Accordingly, there is ongoing research tocreate new and more effective herbicides.

U.S. Pat. No. 4,512,797 describes certain herbicidal 1,3,5-triazinonecompounds. However, that patent does; not disclose the compounds of thepresent invention and does not disclose any preemergenceweed/post-transplant rice applications.

It is therefore an object of the present invention to provide compoundswhich are highly effective for controlling undesirable plant species.

It is also an object of the present invention to provide methods forcontrolling undesirable plant species.

It is a feature of the present invention to provide a method for thecontrol of undesirable plant species in the presence of transplantedrice.

These and other objects and features of the present invention willbecome more apparent from the detailed description thereof set forthbelow.

SUMMARY OF THE INVENTION

The present invention describes 3-(3-aryloxyphen-yl)-1-(substitutedmethyl)-s-triazine-2,4,6-oxo or thiotrione compounds which are useful asherbicidal agents.

The 3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo orthiotrione compounds of the present invention have the structuralformula I ##STR2## wherein Ar is ##STR3## M is CX₄ or N; X, X₁, X₂, X₃,X₄ and Y₁ are each independently hydrogen, halogen, nitro, cyano, C₁ -C₄alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy or S(O)_(m) R₅;

m is an integer of 0, 1 or 2;

R₅ is C₁ -C₄ alkyl or C₁ -C₄ haloalkyl;

R₄ is C₁ -C₄ alkyl;

Y is hydrogen or halogen;

A, A₁ and A₂ are each independently O or S;

R is hydrogen, C₁ -C₄ alkyl, C₂ -C₆ alkoxyalkyl, C₃ -C₁₂alkylcarbonylalkyl, C₃ -C₁₂ haloalkylcarbonylalkyl, C₃ -C₁₂alkoxycarbonylalkyl, C₃ -C₁₂ haloalkoxycarbonylalkyl, C₃ -C₆ alkenyl, C₃-C₆ alkynyl, an alkali metal or phenyl optionally substituted with oneto three halogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxygroups;

R₁ is hydrogen, C₁ -C₄ alkyl or phenyl optionally substituted with oneto three halogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxygroups, and when taken together with R₂, R₁ R₂ may represent thestructure: --(CH₂)_(p) -- where p is an integer of 2, 3, 4 or 5, andwhen n is 0, R₁ may be taken together with R₁₀ to form a ring in whichR₁ R₁₀ is represented by the structure: --(CH₂)_(q) -- where q is aninteger of 2 or 3;

R₂ is hydrogen or C₁ -C₄ alkyl, and when taken together with R₁, R₂ R₁may represent the structure: --(CH₂)_(p) -- where p is an integer of 2,3, 4 or 5;

R₃ is hydrogen or C₁ -C₄ alkyl;

n is an integer of 0, 1 or 2;

V is C(O)R₆, C(W)R₇, CH₂ OC(O)R₈ or CH(OR₉)₂ ;

R₆ is OH, OR₁₀, SR₁₀ or NR₁₁ R₁₂ ;

W is O, NOR₁₁, NCOR₁₁ or NNHCONH₂ ;

R₇ and R₈ are each independently hydrogen or C₁ -C₄ alkyl;

R₉ is C₁ -C₄ alkyl;

R₁₀ is C₁ -C₆ alkyl optionally substituted with C₁ -C₄ alkoxy, C₁ -C₄alkylthio, C₂ -C₆ alkoxycarbonylalkyl, halogen, hydroxy, C₃ -C₆cycloalkyl, tetrahydrofuryl, furyl or phenyl optionally substituted withone or more halogen, cyano, nitro, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁-C₄ alkoxy or C₁ -C₄ haloalkoxy groups,

C₃ -C₆ alkenyl optionally substituted with C₁ -C₄ alkoxy, halogen, C₃-C₆ cycloalkyl or phenyl optionally substituted with one or morehalogen, cyano, nitro, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy orC₁ -C₄ haloalkoxy groups,

C₃ -C₆ alkynyl optionally substituted with C₁ -C₄ alkoxy or halogen,

C₃ -C₆ cycloalkyl,

N═C(R₇ R₈), or

an alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt,silver, nickel, ammonium or organic ammonium cation, and when n is 0,R₁₀ may be taken together with R₁ to form a ring in which R₁₀ R₁ isrepresented by the structure: --(CH₂)_(q) -- where q is an integer of 2or 3; and

R₁₁ and R₁₂ are each independently hydrogen, C₁ -C₆ alkyl, C₂ -C₆alkoxycarbonylalkyl,

benzyl optionally substituted with one or more halogen, cyano, nitro, C₁-C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups,or

phenyl optionally substituted with one or more halogen, cyano, nitro, C₁-C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups.

This invention also relates to compositions containing those compoundsand methods for using those compounds and compositions. Advantageously,it has been found that the compounds of the present invention, andcompositions containing them, are useful for the control of undesirableplant species. The compounds of the present invention are especiallyuseful for the selective control of undesirable plant species in thepresence of crop plants.

DETAILED DESCRIPTION OF THE INVENTION

The present invention provides a method for controlling undesirableplant species which comprises applying to the foliage of said plants orto the soil or water containing seeds or other propagating organsthereof, a herbicidally effective amount of a formula I,3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo orthiotrione compound.

The present invention also provides a method for the control ofundesirable plant species in transplanted rice which comprises applyingto the soil or water containing seeds or other propagating organs ofsaid undesirable plant species, after the rice has been transplanted, aherbicidally effective amount of a formula I,3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo orthiotrione compound.

The 3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo orthiotrione compounds of the present invention have the structuralformula I ##STR4## wherein Ar, Y, Y₁, A, A₁, A₂, R, R₁, R₂, R₃, n and Vare as described above.

Preferred formula I compounds of this invention are those wherein

Ar is ##STR5## M is CX₄ or N; X is hydrogen, halogen, nitro, cyano, C₁-C₄ alkyl or C₁ -C₄ haloalkyl;

X₁ is hydrogen, halogen, nitro or C₁ -C₄ alkyl;

X₂ is hydrogen, halogen, nitro, cyano, C₁ -C₄ haloalkyl or S(O)_(m) R₅ ;

m is an integer of 0 or 1;

R₄ and R₅ are each independently C₁ -C₄ alkyl;

X₃ is hydrogen, halogen or C₁ -C₄ alkoxy;

X₄ is hydrogen or halogen;

Y is hydrogen or F;

Y₁ is hydrogen, halogen, nitro or cyano;

A, A₁ and A₂ are O;

R is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxymethyl, (C₁ -C₄alkoxy)carbonylmethyl, allyl or propargyl;

R₁ is hydrogen or C₁ -C₄ alkyl, and when n is 0, R₁ may be takentogether with R₁₀ to form a ring in which R₁ R₁₀ is represented by thestructure: --(CH₂)₂ --;

R₂ and R₃ are hydrogen;

n is an integer of 0, 1 or 2;

V is C(O)R₆ ;

R₆ is OH, OR₁₀ or NR₁₁ R₁₂ ;

R₁₀ is C₁ -C₆ alkyl optionally substituted with halogen or2-tetrahydrofuryl, or

an alkali metal, ammonium or organic ammonium cation, and

when n is 0, R₁₀ may be taken together with R₁ to form a ring in whichR₁₀ R₁ is represented by the structure: --(CH₂)₂ --; and

R₁₁ and R₁₂ are each independently hydrogen, C₁ -C₆ alkyl or C₁ -C₄alkoxycarbonylmethyl.

More preferred herbicidal agents of the present invention are thosehaving the structural formula II ##STR6## wherein M is CX₄ or N;

X is halogen;

X₂ is halogen or C₁ -C₄ haloalkyl;

X₄ is hydrogen or halogen;

Y₁ is halogen, nitro or cyano;

R is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxymethyl, (C₁ -C₄alkoxy)carbonylmethyl or allyl;

R₁ is hydrogen or C₁ -C₄ alkyl;

R₆ is OH or OR₁₀ ; and

R₁₀ is C₁ -C₆ alkyl or

an alkali metal, ammonium or organic ammonium cation.

Compounds of this invention which are especially useful for the controlof undesirable plant species are those having the stuctural formula IIwherein

M is CX₄ or N;

X is Cl;

X₂ is Cl or CF₃ ;

X₄ is hydrogen or F;

Y₁ is F, Cl, Br, nitro or cyano;

R is hydrogen, C₁ -C₄ alkyl, (C₁ -C₄ alkoxy)carbonylmethyl or allyl;

R₁ is hydrogen or C₁ -C₄ alkyl;

R₆ is OR₁₀ ; and

R₁₀ is C₁ -C₆ alkyl.

3-(3-Aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-trionecompounds of the present invention which are particularly effectiveherbicidal agents include

methyl 3-{2-bromo-5-(2-chloro-α,α,α,6-tetrafluoro,-p-tolyl)oxy!phenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate;

methyl 3-{5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!-2-fluorophenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate;

methyl 3-{2-chloro-5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!phenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate;

dimethyl 5-5-(2,4-dichlorophenoxy)-2-nitrophenyl!dihydro-2,4,6-trioxo-s-triazine-1,3(2H,.4H)-diacetate;

methyl 3-{5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!-2-nitrophenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate;

methyl 3-{5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate;

methyl 3-{2-bromo-5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!phenyl}tetrahydro-α,5-dimethyl-2,4,6-trioxo-s-triazine-1(2H)-acetate;

ethyl 3-{5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenyl}tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate;

ethyl 3-{5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!-2-cyanophenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate;

methyl 3-5-(2,4-dichlorophenoxy)-2-nitrophenyl!tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate;

methyl 3-{5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenyl}tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate;

ethyl 3-allyl-5-{5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenyl}tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate;and

tert-butyl 3-{5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!-2-nitrophenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate,among others.

Exemplary of halogen hereinabove are flourine, chlorine, bromine andiodine. The terms C_(l) -C₄ haloalkyl and C₁ -C₄ haloalkoxy as used inthe specification and claims designates a C₁ -C₄ alkyl group or a C₁ -C₄alkoxy group substituted with one or more halogen atoms, respectively.In formula I above, alkali metals include: sodium, potassium andlithium. Alkaline earth metals of formula I include magnesium andcalcium. Further, the term organic ammonium is defined as a groupconsisting of a positively charged nitrogen atom joined to from one tofour aliphatic groups, each containing from one to sixteen carbon atoms.

Advantageously, it has now been found that certain compounds of thepresent invention are especially useful for the selective control ofundesirable plant species in the presence of important agronomic crops.

Compounds of formula I wherein A, A₁ and A₂ are O and V is CO₂ R₁₀ maybe prepared by reacting a 3-aryloxybenzoic acid of formula III withthionyl chloride to form a 3-aryloxybenzoyl chloride compound of formulaIV, reacting the formula IV compound with ammonium hydroxide to form a3-aryloxybenzamide compound of formula V, reacting the formula Vcompound with sodium hypochlorite and sodium hydroxide to form anintermediate isocyante compound of formula VI, reacting the formula VIcompound with an amine of formula. VII to form a1-(3-aryloxyphenyl)-3-substituted methylurea of formula VIII andcyclizing the formula VIII compound with N-(chlorocarbonyl) isocyanateto form the desired formula I compound and optionally alkylating theformula I compound wherein R is hydrogen with an alkylating agent offormula IX and a base. The reaction scheme is shown in Flow Diagram I.##STR7##

Alternatively, compounds of formula I wherein A, A₁, and A₂ are O, V isCO₂ R₁₀ and R is other than hydrogen or an alkali metal may be preparedby reacting a formula VI isocyanate with an amine of formula X to form aurea compound of formula XI, cyclizing the formula XI compound withN-(chlorocarbonyl) isocyanate to form a1-(3-aryloxyphenyl)-s-triazine-2,4,6-(1H,3H,5H)-trione compound offormula XII and alkylating the formula XII compound with an alkylatingagent of formula XIII and a base to form the desired formula I compound.The above reactions are shown in Flow Diagram II. ##STR8##

Formula I compounds wherein A, A₁ and A₂ are O and V is CO₂ R₁₀ may alsobe prepared by reacting a 3-fluorobenzoic acid of formula XIV withthionyl chloride to form a 3-fluorobenzoyl chloride compound of formulaXV, reacting the formula XV compound with sodium azide to form a3-fluorobenzoyl azide compound of formula XVI, heating the formula XVIcompound to form an intermediate isocyanate compound of formula XVII,reacting the isocyanate compound with an amine of formula VII to form a1-(3-fluorophenyl)-3-(substituted methyl)urea of formula XVIII,cyclizing the formula XVIII compound with N-(chlorocarbonyl) isocyanateto form a 1-(3-fluorophenyl)-3-(substitutedmethyl)-s-triazine-2,4,6-trione compound of formula XIX and reacting theformula XIX compound with an alcohol of formula XX and a base to formthe desired formula I compound and optionally alkylating the formula Icompound with an alkylating agent of formula IX and a base. The abovereactions are shown below in Flow Diagram III. ##STR9##

Alternatively, compounds of formula I wherein A, A₁ and A₂ are O, V isCO₂ R₁₀ and R is other than hydrogen or an alkali metal may be preparedby cyclizing a urea of formula XXI with N-(chlorocarbonyl) isocyanate toform a 1-(3-methoxyphenyl)-s-triazine-2,4,6-trione compound of formulaXXII, reacting the formula XXII compound with a Lewis or protic acidsuch as boron tribromide to form a1-(3-hydroxyphenyl)-s-triazine-2,4,6-trione compound of formula XXIII,reacting the formula XXIII compound with a fluoroaryl compound offormula XXIV and a base to form a1-(3-aryloxyphenyl)-s-triazine-2,4,6-trione compound of formula XXV andalkylating the formula XXV compound with an alkylating agent of formulaXIII and a base to form the desired formula I compound. The reactionscheme is shown in Flow Diagram IV. ##STR10##

Compounds of formula I wherein A, A₁ and A₂ are O, V is CO₂ R₁₀ and R isother than hydrogen or an alkali metal may also be prepared by cyclizinga urea of formula XXVI with N-(chlorocarbonyl) isocyanate to form a1-(3-methoxyphenyl)-3-(substituted methyl)-s-triazine-2,4,6-trionecompound of formula XXVII, reacting the formula XXVII compound with analkylating agent of formula IX and a base to form a1-(3-methoxyphenyl)-3-(substitutedmethyl)-5-substituted-s-triazine-2,4,6-trione compound of formulaXXVIII, reacting the formula XXVIII compound with a Lewis or protic acidsuch as boron tribromide to form a 1-(3-hydroxyphenyl)-3-(substitutedmethyl)-5-substituted-s-triazine-2,4,6-trione compound of formula XXIXand reacting the formula XXIX compound with a fluoroaryl compound offormula XXIV and a base to form the desired formula I compound. Thereactions are shown in Flow Diagram V. ##STR11##

Compounds of formula I wherein A and A₂ are O, A₁ is S and V is CO₂ R₁₀may be prepared by reducing a 3-(aryloxy)nitrobenzene of formula XXX toform a 3-(aryloxy)aminobenzene compound of formula XXXI, reacting theformula XXXI compound with an isocyanate of formula XXXII to form a1-(3-aryloxyphenyl)-3-(substituted methyl)urea compound of formula VIII,reacting the formula VIII compound with an isothiocyanate of formulaXXXIII to form an intermediate compound of formula XXXIV, and cyclizingthe formula XXXIV compound with base to form the desired formula Icompound and optionally alkylating the formula I compound wherein R ishydrogen with an alkylating agent of formula IX and a base. Thereactions are shown in Flow Diagram VI. ##STR12##

Alternatively, compounds of formula I wherein A and A₂ are O. A₁ is Sand V is CO₂ R₁₀ may be prepared by reacting a formula XXXI compoundwith an isocyanate of formula XXXV to form a urea of formula XI,reacting the formula XI compound with an isothiocyanate of formulaXXXIII to form an intermediate compound of formula XXXVI, cyclizing theformula XXXVI compound with base to form a1-(3-aryloxyphenyl)-s-triazine-2,6-dioxo-4-thione compound of formulaXXXVII, and alkylating the formula XXXVII compound with an alkylatingagent of formula XIII and a base to form the desired formula I compound.The reaction scheme is shown below in Flow Diagram VII. ##STR13##

Compounds of formula I wherein A and A₁ are O, A₂ is S and V is CO₂ R₁₀may be prepared by reacting a compound of formula XXXI with anisothiocyanate of formula XXXVIII to form a thiourea of formula XXXIX,and cyclizing the formula XXXIX compound with N-(chlorocarbonyl)isocyanate to form the desired formula I compound and optionallyalkylating the formula I compound wherein R is hydrogen with analkylating agent of formula IX and a base. The reactions are shown inFlow Diagram VIII. ##STR14##

Compounds of formula I wherein A is S, A₁ and A₂ are O, and V is CO₂ R₁₀may be prepared by reacting a compound of formula XXXI with anisothiocyanate of formula XL to form a thiourea of formula XLI,cyclizing the formula XLI compound with N-(chlorocarbonyl) isocyanate toform a 1-(3-aryloxyphenyl)-s-triazine-4,6-dioxo-2-thione compound offormula XLII, and alkylating the formula XLII compound with analkylating agent of formula XIII and a base to form the desired formulaI compound. The reaction scheme is shown in Flow Diagram IX. ##STR15##

Compounds of formula I wherein A₁ and A₂ are S, A is O or S and V is CO₂R₁₀ may be prepared by reacting a compound of formula XXXIX with anisothiocyanate of formula XL to form an intermediate compound of formulaXLIII, and cyclizing the formula XLIII compound with phosgene orthiophosgene to form the desired formula I compound. The reactions areshown below in Flow Diagram X. ##STR16##

Compounds of formula I wherein A and A₁ are S, A₂ is O or S and V is CO₂R₁₀ may be prepared by reacting a compound of formula XLI with anisothiocyanate of formula XXXVIII to form an intermediate compound offormula XLIV, and cyclizing the formula XLIV compound with phosgene orthiophosgene to form the desired formula I compound. The reaction schemeis shown in Flow Diagram XI. ##STR17##

Compounds of formula I wherein A and A₂ are S, A₁ is O and V is CO₂ R₁₀may be prepared by reacting a compound of formula XXXIX with anisocyanate of formula XXXV to form an intermediate compound of formulaXLV, and cyclizing the formula XLV compound with thiophosgene to formthe desired formula I compound. The reactions are shown in Flow DiagramXII. ##STR18##

Alternatively, compounds of formula I wherein A and A₂ are S, A₁ is Oand V is CO₂ R₁₀ may be prepared by reacting a compound of formula XLIwith an isocyanate of formula XXXII to form an intermediate compound offormula XLVI, and cyclizing the formula XLVI compound with thiophosgeneto form the desired formula I compound. The reaction scheme is shown inFlow Diagram XIII. ##STR19##

Compounds of formula I wherein R₆ is NR₁₁ R₁₂ may be prepared usingstandard procedures such as hydrolyzing the appropriate ester of formulaXLVII in the presence of trifluoroacetic acid, reacting the resultantacid with thionyl chloride to give the acid chloride of formula XLVIIIand reacting the formula XLVIII acid chloride with an amine of formulaXLIX optionally in the presence of base to give the desired product. Thereactions are shown in Flow Diagram XIV. ##STR20##

Using the formula XLVIII acid chloride, formula I compounds wherein V isC(O)R₇ may be prepared as shown below in Flow Diagram XV. ##STR21##

Formula I compounds wherein R₆ is SR₁₀ may be prepared by reacting theformula XLVIII acid chloride with a thiol of formula L. The reaction isshown below in Flow Diagram XVI. ##STR22##

Formula I compounds wherein V is CH₂ OC(O)R₈ may be prepared by reducinga compound of formula LI to form an alcohol of formula LII, and reactingthe formula LII compound with an acid halide of formula LIII in thepresence of a base. The reactions are shown below in Flow Diagram XVII.##STR23##

Formula I compounds wherein V is CHO or CH(OR₉)₂ may be prepared byreducing the formula LI compound to form an aldehyde of formula LIV, andreacting the formula LIV aldehyde with an alcohol of formula LV in thepresence of an acid. The reactions are shown in Flow Diagram XVIII.##STR24##

Compounds of formula I wherein V is HC═NOR₁₁ may be prepared by reactingthe formula LIV aldehyde with an amine of formula LVI. The reaction isshown in Flow Diagram XIX. ##STR25##

Similarly, compounds of formula I wherein V is HC═NCOR₁₁ or HC═NNHCONH₂may be prepared by reacting the formula LIV aldehyde with an amine offormula LVII or a semicarbazide of formula LVIII. The reactions areshown below in Flow Diagram XX. ##STR26##

Formula I compounds wherein R₁₀ is an alkali metal, alkaline earthmetal, manganese, copper, zinc, cobalt, silver, nickel, ammonium ororganic ammonium cation, and/or R is an alkali metal, may be preparedfrom formula I compounds wherein R₆ is OH and/or R is hydrogen byconventional processes known to those skilled in the art.

Starting formula XXI and XXVI compounds may be prepared as shown belowin Flow Diagram XXI. ##STR27##

Starting formula XXI compounds wherein Y is hydrogen and Y₁ is cyano maybe prepared as shown below in Flow Diagram XXII. ##STR28##

Compounds of formula XXXI, which are described in Flow Diagram VI, mayalso be prepared as shown in Flow Diagram XXIII. ##STR29##

This invention also relates to intermediate compounds which are usefulin the preparation of the formula I compounds. The intermediatecompounds have the structural formulas LIX, LX and LXI. ##STR30##wherein T is F, OH or OCH₃ ;

T₁ is OH or OCH₃ ;

T₂ is F, OCH₃, ##STR31## M is CX₄ or N; X, X₁, X₂, X₃, X₄ and Y₁ areeach independently hydrogen, halogen, nitro, cyano or C₁ -C₄ haloalkyl;

Y is hydrogen or halogen;

R₄ is C₁ -C₄ alkyl;

R is hydrogen, C₁ -C₄ alkyl, C₂ -C₆ alkoxyalkyl, C₃ -C₁₂-alkylcarbonylalkyl, C₃ -C₁₂ haloalkylcarbonylalkyl, C₃ -C₁₂alkoxycarbonylalkyl, C₃ -C₁₂ haloalkoxycarbonylalkyl, C₃ -C₆ alkenyl orC₃ -C₆ alkynyl;

R₁, R₂ and R₃ are each independently hydrogen or C₁ -C₄ alkyl;

n is an integer of 0, 1 or 2; and

R₁₀ is C₁ -C₆ alkyl.

The present invention also relates to intermediate compounds having thestructural formula LXI ##STR32## wherein Ar is ##STR33## M is CX₄ or N;X, X₁, X₂, X₃, X₄ and Y₁ are each independently hydrogen, halogen,nitro, cyano or C₁ -C₄ haloalkyl;

R₄ is C₁ -C₄ alkyl; and

R is C₃ -C₁₂ alkylcarbonylalkyl, C₃ -C₁₂ haloalkylcarbonylalkyl, C₃ -C₁₂alkoxycarbonylalkyl or C₃ -C₁₂ haloalkoxycarbonylalkyl.

The formula I compounds of the present invention are effectiveherbicidal agents useful for the control of a wide variety ofundesirable plant species. Those compounds are effective for controllingweeds native to both dry land and wet land areas. The compounds are alsouseful as aquatic herbicides and are effective in controlling theabove-said plants when applied to the foliage thereof or to soil orwater containing seeds or other propagating organs thereof such asstolons, tubers or rhizomes, at rates of from about 0.016 to 4.0 kg/haand preferably from about 0.032 to 2.0 kg/ha.

Advantageously, it has been found that the formula I compounds of thepresent invention are effective for controlling undesirable plantspecies including important weeds in transplanted rice culture. Thecompounds may be applied to the soil or water containing transplantedrice plants and seed or other propagating organs of a variety of weedspecies.

The formula I compounds of this invention are best suited for use asbroad spectrum herbicides, especially when applied postemergence to thelocus in which weed control is desired. However, certain compounds ofthis invention are selective. In fact, some of the compounds of thisinvention are selective in crops such as soybeans, rice, wheat and cornwhen applied as preemergence and/or postemergence treatments.

While the formula I compounds of this invention are effective forcontrolling undesirable plant species when employed alone, they may alsobe used in combination with other biological chemicals, including otherherbicides.

The formula I compounds of this invention may be applied to crops in theform of a solid or liquid herbicidal composition, comprising aherbicidally effective amount of the compound dispersed or dissolved inan agronomically acceptable, inert solid or liquid carrier. Thecompositions may be applied as preemergence or postemergence treatments.

The formula I compounds may be formulated as emulsifiable concentrates,wettable powders, granular formulations, flowable concentrates and thelike.

In order to facilitate a further understanding of the invention, thefollowing examples are presented primarily for the purpose ofillustrating more specific details thereof. The invention should not bedeemed limited by the examples as the full scope of the invention isdefined in the claims. The term NMR designates nuclear magneticresonance spetroscopy.

EXAMPLE 1 Preparation of 5-Fluoro-2-nitrobenzoyl chloride ##STR34##

A mixture of 5-fluoro-2-nitrobenzoic acid (47.51 g, 0.257 mol) andthionyl chloride (100 mL, 1.370 mol) is refluxed for several hours andconcentrated in vacuo to give the title product which is used in Example2 without further purification.

Using essentially the same procedure, but using the appropriatelysubstituted benzoic acid, the following compounds are obtained:

    ______________________________________                                         ##STR35##                                                                    ______________________________________                                        Br                                                                            CN                                                                            NO.sub.2                                                                      ______________________________________                                    

EXAMPLE 2 Preparation of 5-Fluoro-2-nitrobenzoyl azide ##STR36##

A solution of 5-fluoro-2-nitrobenzoyl chloride (52 g, 0.256 mol) in atoluene (50 mL) and acetone (60 mL) mixture is added dropwise to asolution of sodium azide (19.55 g, 0.301 mol) in water while maintainingthe reaction mixture temperature below 30° C. The resultant solid iscollected and the filtrate is extracted with ether. The organic extractsare combined, washed with water, dried over anhydrous magnesium sulfateand concentrated by blowing air over the solution to obtain additionalsolids. The solids are combined, slurried in an acetone/water (1:3)solution, filtered and dried to give the title product as a yellowsolid.

EXAMPLE 3 Preparation of N- (5-Fluoro-2-nitrophenyl)carbamoyl!glycinemethyl ester ##STR37##

A solution of 5-fluoro-2-nitrobenzoyl azide (5.46 g, 0.026 mol) intoluene is stirred at 65° C. for 90 minutes, cooled, treated withglycine methyl ester hydrochloride (3.63 g, 0.029 mol), stirred for 10minutes, treated with pyridine (5 mL, 0.062 mol), stirred overnight,diluted with water and extracted with ethyl acetate. The organicextracts are combined, washed sequentially with water, 0.4M hydrochloricacid and brine, dried over anhydrous magnesium sulfate and concentratedin vacuo to obtain a solid. The solid is slurried in an ether/hexanes(6:4) solution, filtered and dried to give a yellow solid. Columnchromatography of the yellow solid using silica gel and ethyl acetate inhexanes solutions gives the title product as a yellow solid, mp133.2°-135.30° C.

EXAMPLE 4 Preparation of N-(4,5-Difluoro-2-nitrophenyl)carbamoyl!glycine methyl ester ##STR38##

A solution of 4,5-difluoro-2-nitroaniline (1.07 g, 6.15 mmol) intetrahydrofuran is cooled to 2° C., treated with phosgene (3.8 mL,1.93M, 7.33 mmol), stirred at ice-bath temperature for 2 hours, treatedwith glycine methyl ester hydrochloride (1.02 g, 8.12 mmol), treatedwith pyridine (1 mL, 12.64 mmol), stirred at room temperature for 3days, diluted with concentrated ammonia solution and water, andextracted with ethyl acetate. The organic extracts are combined, washedsequentially with water and brine, dried over anhydrous magnesiumsulfate and concentrated in vacuo to obtain a residue. Columnchromatography of the residue using silica gel and an ethylacetate/hexanes (1:3) solution gives the title product as a solid, mp118.9°-122.9° C.

EXAMPLE 5 Preparation of Methyl3-(5-fluoro-2-nitrophenyl)tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate##STR39##

A solution of N- (5-fluoro-2-nitrophenyl)carbamoyl!glycine methyl ester(20.47 g, 75.46 mmol) in methylene chloride is cooled in an ice-bath,treated with N-(chlorocarbonyl) isocyanate 7 mL, 86.94 mmol), treateddropwise with pyridine (7.5 mL, 92.92 mmol), warmed to and stirred atroom temperature for 90 minutes, and filtered. The filtrate is pouredinto 0.11M hydrochloric acid (450 mL), the phases are separated and theaqueous phase is extracted with methylene chloride. The organic phaseand extracts are combined, washed with brine, dried over anhydrousmagnesium sulfate and concentrated in vacuo to obtain the title productas a yellow solid.

Using essentially the same procedure, but substituting N-(4,5-difluoro-2-nitrophenyl)carbamoyl!glycine methyl ester for N-(5-fluoro-2-nitrophenyl)carbamoyl!glycine methyl ester, methyl3-(4,5-difluoro-2-nitrophenyl)tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetateis obtained as a yellow oil.

EXAMPLE 6 Preparation of Methyl 3-5-(2,4-dichlorophenoxy)-2-nitrophenyl!tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate##STR40##

Potassium carbonate (1.14 g, 8.25 mmol) is added to a solution of methyl3-(5-fluoro-2-nitrophenyl)tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate(0.93 g, 2.74 mmol) and 2,4-dichlorophenol (0.66 g, 4.07 mmol) inN,N-dimethylformamide at 38° C. The reaction mixture is stirred at 38°C. for 3 days, cooled to room temperature and poured into 1Mhydrochloric acid. The aqueous mixture is extracted with ethyl acetate.The organic extracts are combined, washed sequentially with water andbrine, dried over anhydrous magnesium sulfate and concentrated in vacuoto obtain an orange oil. Column chromatography of the oil using silicagel and 30% to 40% ethyl acetate in hexanes solutions gives the titleproduct as a yellow foam which is identified by NMR spectral analysis.

EXAMPLE 7 Preparation of Methyl 3-5-(2,4-dichlorophenoxy)-2-nitrophenyl!tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate##STR41##

Methyl iodide (0.15 mL, 2.41 mmol) and potassium carbonate (0.19 g, 1.34mmol) are added to a solution of methyl 3-5-(2,4-dichlorophenoxy)-2-nitrophenyl!tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate(0.40 g, 0.83 mmol) in N,N-dimethylformamide. The reaction mixture isstirred overnight at room temperature and poured into a saturatedammonium chloride solution. The aqueous mixture is extracted with ethylacetate. The organic extracts are combined, washed sequentially withwater and brine, dried over anhydrous magnesium sulfate and concentratedin vacuo to obtain a yellow oil. Column chromatography of the oil usingsilica gel and an ethyl acetate/hexanes (1:3) solution gives the titleproduct as a yellows foam which is identified by NMR spectral analysis.

Using essentially the same procedure, the following compounds areobtained:

    ______________________________________                                         ##STR42##                                                                    X     X.sub.2  Y.sub.1                                                                              R          R.sub.10                                                                           mp °C.                           ______________________________________                                        H     Cl       NO.sub.2                                                                             CH.sub.2 CO.sub.2 CH.sub.3                                                               CH.sub.3                                     H     CF.sub.3 NO.sub.2                                                                             CH.sub.3   C.sub.2 H.sub.5                                                                    75-77                                   H     CF.sub.3 NO.sub.2                                                                             CH.sub.2 CHCH.sub.2                                                                      C.sub.2 H.sub.5                              F     CF.sub.3 CN     CH.sub.3   C.sub.2 H.sub.5                                                                    86-88                                   F     CF.sub.3 CN     CH.sub.2 CO.sub.2 CH.sub.3                                                               C.sub.2 H.sub.5                                                                    92-94                                   H     CF.sub.3 NO.sub.2                                                                             CH.sub.2 CO.sub.2 CH.sub.3                                                               C.sub.2 H.sub.5                                                                    61-65                                   H     CF.sub.3 NO.sub.2                                                                             CH.sub.2 CHCH                                                                            C.sub.2 H.sub.5                                                                    65-70                                   ______________________________________                                    

EXAMPLE 8 Preparation of Methyl3-(5-fluoro-2-nitrophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate##STR43##

Methyl iodide (5.0 mL, 80.31 mmol) and potassium carbonate (11.12 g,80.45 mmol) are added to a solution of methyl3-(5-fluoro-2-nitrophenyl)tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate(25.65 g, 75.40 mmol) in N,N-dimethylformamide. The reaction mixture isstirred at room temperature overnight, concentrated in vacuo and pouredinto water. The aqueous mixture is extracted with ethyl acetate. Theorganic extracts are combined, washed sequentially with water, 0.08Msodium metabisulfite solution and brine, dried over anhydrous magnesiumsulfate and concentrated in vacuo to obtain a yellow oil. The oil isdissolved in a refluxing ethyl acetate/ether (1:1) solution and theresultant solution is chilled end treated dropwise with hexanes toobtain a solid. The solid is collected, washed with an ether/ethylacetate/hexanes (1:1:8) solution and dried overnight in vacuo at 50° C.to give the title product as a solid, mp 121.8°-122.3° C.

Using essentially the same procedure, but substituting methyl3-(4,5-difluoro-2-nitrophenyl)tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetatefor methyl3-(5-fluoro-2-nitrophenyl)tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate,methyl3-(4,5-difluoro-2-nitrophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetateis obtained.

EXAMPLE 9 Preparation of Methyl 3-{5-(2,4-dichloro-m-tolyl)oxy!-2-nitrophenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate##STR44##

A mixture of methyl3-(5-fluoro-2-nitrophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate(0.51 g, 1.4 mmol), 2,4-dichloro-3-methylphenol (0.33 g, 1.9 mmol) andpotassium carbonate (0.28 g, 2.0 mmol) in N,N-dimethylformamide isstirred overnight at room temperature and poured into water. The aqueousmixture is extracted with ethyl acetate. The organic extracts arecombined, washed sequentially with water, 1M sodium hydroxide solution,water and brine, dried over anhydrous magnesium sulfate and concentratedin vacuo to obtain a yellow solid. The solid is slurried with anether/hexanes (1:1) solution, filtered and dried in vacuo to give thetitle product as a yellow solid, mp 199.9°-202° C.

Using essentially the same procedure, but using the appropriatelysubstituted phenol, the following compounds are obtained:

    ______________________________________                                         ##STR45##                                                                    X     X.sub.1 X.sub.2  X.sub.3                                                                            X.sub.4                                                                              Y   mp °C.                          ______________________________________                                        H     H       F        H    CF.sub.3                                                                             H                                          Cl    H       Cl       H    Cl     H   199.9-201.4                            Cl    H       SCH.sub.3                                                                              H    H      H   192.8-193.6                            Cl    H       Cl       H    CH.sub.3                                                                             H   180.4-182.5                            NO.sub.2                                                                            H       H        H    H      H                                          H     H       H        Cl   Cl     H     169-170.2                            H     H       Cl       H    F      H   193.1-193.8                            H     H       NO.sub.2 H    F      H   193-197                                H     Cl      H        Cl   Cl     H   230.5-231.9                            CN    H       H        H    H      H   175.7-176.2                            Cl    Cl      Cl       H    H      H   216-217                                H     H       NO.sub.2 H    H      H   196.8                                  F     F       F        H    H      H   160.2-166.4                            H     OCH.sub.3                                                                             Cl       H    Cl     H   207.3-207.7                            H     F       F        H    F      H   142.2-144.2                            H     Cl      Cl       H    Cl     H                                          H     H       CN       H    H      H   210.7                                  H     Cl      H        Cl   H      H                                          Cl    H       H        H    Cl     H                                          H     H       Cl       H    H      H   191.2-192                              Cl    H       H        H    H      H   161.3-168.4                            Cl    H       Cl       H    H      F                                          ______________________________________                                    

EXAMPLE 10 Preparation of Methyl 3-{2-chloro-4-(methylsulfinyl)phenoxy!-2-nitrophenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate##STR46##

3-Chloroperoxybenzoic acid (0.17 g, 0.77 mmol) is added to a solution ofmethyl 3-{5-2-chloro-4-(methylthio)phenoxy!-2-nitrophenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate(0.29 g, 0.56 mmol) in methylene chloride which is previously cooled inan ice-bath. The reaction mixture is stirred at ice-bath temperature for90 minutes, quenched with sodium metabisulfite solution (0.2M, 10 mL)and poured into saturated sodium bicarbonate solution. The aqueousmixture is concentrated in vacuo to remove methylene chloride, cooledand extracted with ethyl acetate. The organic extracts are combined,washed sequentially with Water and brine, dried over anhydrous magnesiumsulfate and concentrated in vacuo to obtain a yellow oil. Columnchromatography of the oil using silica gel and a 2% methanol inmethylene chloride solution gives the title product as a white foamwhich is identified by NMR spectral analysis.

EXAMPLE 11 Preparation of Methyl tetrahydro-3-methyl-5-2-nitro-5-(2-pyridyloxy)phenyl!-2,4,6-trioxo-s-triazine-1(2H)-acetate##STR47##

A mixture of methyl3-(5-fluoro-2-nitrophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate(0.55 g, 1.55 mmol), 2-hydroxypyridine (0.25 g, 2.58 mmol) and potassiumcarbonate (0.37 g, 2.64 mmol) in N,N-dimethylformamide is stirred atroom temperature overnight and poured into water. The aqueous mixture isextracted with ethyl acetate. The organic extracts are combined, washedsequentially, with water, 0.2M sodium hydroxide solution, water andbrine, dried over anhydrous magnesium sulfate and concentrated in vacuoto obtain a yellow foam. Column chromatography of the foam using silicagel and a 2% methanol in methylene chloride solution gives the titleproduct as a yellow oil which is identified by NMR spectral analysis.

EXAMPLE 12 Preparation of 5-Methoxy-2-nitrobenzaldehyde ##STR48##

Methyl iodide (23.34 g, 0.165 mol) and potassium carbonate (22.73 g,0.165 mol) are added to a solution of 5-hydroxy-2-nitrobenzaldehyde (25g, 0.149 mol) in N,N-dimethylformamide. The reaction mixture is stirredat room temperature for 18 hours and poured into water. The resultantaqueous mixture is extracted with ethyl acetate. The organic extractsare combined, washed with brine, dried over anhydrous sodium sulfate andconcentrated in vacuo to give the title product as a brown solid, mp89°-90° C.

EXAMPLE 13 Preparation of 5-Methoxy-2-nitrobenzoic acid ##STR49##

Sulfamic acid (15.73 g, 0.162 mol) is added to a solution of5-methoxy-2-nitrobezaldehyde (19.6 g, 0.108 mol) in an acetone/water(1:1) mixture. Sodium chlorite (18.31 g, 80% real, 0.162 mol) is thenadded to the reaction mixture at a rate which maintains the reactionmixture temperature below 40° C. The resultant reaction mixture isstirred at room temperature for 24 hours and poured into water. Theaqueous mixture is extracted with ethyl acetate. The organic extractsare combined, washed sequentially with 2N hydrochloric acid and brine,dried over anhydrous magnesium sulfate and concentrated in vacuo to givethe title product as a yellow solid.

Using essentially the same procedure, but substituting2-fluoro-5-methoxybenzaldehyde for 5-methoxy-2-nitrobezaldehyde,2-fluoro-5-methoxybenzoic acid is obtained as a white solid, mp144°-146° C.

EXAMPLE 14 Preparation of 5-Methoxy-2-nitrobenzoyl chloride ##STR50##

A mixture of 5-methoxy-2-nitrobenzoic acid (15.8 g, 0.08 mol), oxalylchloride (25 g, 0.197 mol) and N,N-dimethylformamide (2 drops) isstirred at reflux for 4 hours, cooled, stirred at room temperature undernitrogen for several days and concentrated in vacuo to give the titleproduct as a yellow oil which is identified by ¹ HNMR spectral analysis.

Using essentially the same procedure, but substituting2-cyano-5-methoxybenzoic acid for 5-methoxy-2-nitrobenzoic acid,2-cyano-5-methoxybenzoyl chloride is obtained as a solid, mp 192°-194°C.

EXAMPLE 15 Preparation of 2-Bromo-5-methoxybenzamide ##STR51##

A 30% ammonium hydroxide solution (56 mL) is added dropwise to asolution of 2-bromo-5-methoxybenzoyl chloride in methylene chloride at0° C. After the addition is complete, the reaction mixture is filteredto obtain a solid which is air-dried and recrystallized from amethanol/water solution to give the title product as a white solid, mp158°-159° C.

Using essentially the same procedure, but employing the appropriatelysubstituted benzoyl chloride, the following compounds are obtained:

    ______________________________________                                         ##STR52##                                                                            Y.sub.1                                                                            mp °C.                                                    ______________________________________                                                NO.sub.2                                                                           145-150                                                                  F    120-124                                                                  CN   214-218                                                          ______________________________________                                    

EXAMPLE 16 Preparation of 1-(2-Bromo-5-methoxyphenyl)-3- methylurea##STR53##

A mixture of 2-bromo-5-methoxybenzamide (16 g, 0.070 mol) in methanol iscooled to 0° C., treated with a mixture of 50% sodium hydroxide solution(7 g) and 5% sodium hypochlorite solution (130 mL), stirred at 0° C. for10 minutes, treated with 40% methylamine solution (17.81 mL), stirred at60° C. for 9 hours, cooled and filtered to obtain a solid. The solid iswashed with water and air-dried to give the title product as a whitesolid, mp 164°-166° C.

Using essentially the same procedure, but using the appropriatelysubstituted benzamide, the following compounds are obtained:

    ______________________________________                                         ##STR54##                                                                            Y.sub.1                                                                            mp °C.                                                    ______________________________________                                                NO.sub.2                                                                           209-211                                                                  F    142-145                                                          ______________________________________                                    

EXAMPLE 17 Preparation of1-(2-Bromo-5-methoxyphenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione##STR55##

N-(Chlorocarbonyl) isocyanate (6.85 g, 0.065 mol) is added dropwise to amixture of 1-(2-bromo-5-methoxyphenyl)-3-methylurea (13.4 g, 0.052 mol)in toluene. The reaction mixture is stirred at 60° C. for 2 hours,cooled, stirred overnight at room temperature and filtered to obtain asolid. The solid is washed with ether and air-dried to give the titleproduct as a white solid, mp 185°-187° C.

Using essentially the same procedure, but using the appropriatelysubstituted urea, the following compounds are obtained:

    ______________________________________                                         ##STR56##                                                                            Y.sub.1                                                                            mp °C.                                                    ______________________________________                                                NO.sub.2                                                                           185-188                                                                  F    210-212                                                          ______________________________________                                    

EXAMPLE 18 Preparation of1-(2-Bromo-5-hydroxyphenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione##STR57##

A solution of boron tribromide in methylene chloride (98.75 mL of a 1Msolution in methylene chloride) is added to a mixture of1-(2-bromo-5-methoxyphenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione(14.4 g, 0.438 mol) in methylene chloride at 0° C. The reaction mixtureis stirred at room temperature for 1 hour and filtered to obtain asolid. The solid is washed with water and air-dried to give the titleproduct as a white solid, mp 265°-270° C.

Using essentially the same procedure, but using the appropriatelysubstituted triazine-2,4,6-trione, the following compounds are obtained:

    ______________________________________                                         ##STR58##                                                                    Y.sub.1                                                                       ______________________________________                                        NO.sub.2                                                                      ______________________________________                                    

EXAMPLE 19 Preparation of 1-{2-Bromo-5-3-chloro-5-(trifluoromethyl)-2-pyridyloxy!phenyl}-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione##STR59##

A mixture of1-(2-bromo-5-hydroxyphenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione(5.29 g, 0.0168 mol), 2,3-dichloro-5-trifluoromethylpyridine (5.44 g,0.025 mol) and potassium carbonate (3.45 g, 0.025 mol) inN,N-dimethylformamide is stirred at 80° C. for 18 hours, cooled to roomtemperature and poured into water. The aqueous mixture is extracted withethyl acetate. The organic extracts are combined, washed with brine,dried over anhydrous magnesium sulfate and concentrated in vacuo toobtain a solid. The solid is recrystallized from an ether/hexanessolution to give the title product as a yellow solid, mp 97°-110° C.

Using essentially the same procedure, but using the appropriatelysubstituted fluorobenzene or chloropyridine, the following compounds areobtained:

    ______________________________________                                         ##STR60##                                                                    X         X.sub.2                                                                              M          Y.sub.1                                                                            mp °C.                                ______________________________________                                        H         Cl     CCl        Br   210-212                                      Cl        Cl     N          Br   187-189                                      Cl        CF.sub.3                                                                             CF         NO.sub.2                                                                           225-228                                      ______________________________________                                    

EXAMPLE 20 Preparation of Isopropyl 3-{ 2-bromo-5-{3-chloro-5-(trifluoromethyl)-2-pyridyl!oxy}phenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate##STR61##

A mixture of 1-{2-bromo-5-3-chloro-5-(trifluoromethyl)-2-pyridyloxy!phenyl}-3-methyl-s-triazine-2,4,6-(1H,3H,5H)-trione(0.99 g, 2.01 mmol), isopropyl bromoacetate (0.54 g, 2.98 mmol) andpotassium carbonate (0.41 g, 2.97 mmol) in N,N-dimethylformamide isstirred overnight at room temperature and poured into water. The aqueousmixture is filtered to obtain a solid which is air-dried to give thetitle product as a white solid, mp 60°-65° C.

Using essentially the same procedure, but using the appropriatelysubstituted 3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione and theappropriate electrophile, the following compounds are obtained:

    ______________________________________                                         ##STR62##                                                                    X     X.sub.2                                                                              M        Y.sub.1                                                                             R.sub.13  mp °C.                           ______________________________________                                        Cl    CF.sub.3                                                                             N        Br    CH.sub.2 CO.sub.2 CH.sub.3                                                              85-90                                   Cl    CF.sub.3                                                                             N        Br    CH.sub.2 CONH.sub.2                                                                     263-266                                 H     Cl     CCl      Br    CH.sub.2 CO.sub.2 CH.sub.3                                                              58-65                                   H     Cl     CCl      Br    (CH.sub.2).sub.3 CO.sub.2 CH.sub.3                H     CF.sub.3                                                                             CCl      H     CH.sub.2 CO.sub.2 CH.sub.3                                                              118-120                                 H     CF.sub.3                                                                             CCl      H     CH.sub.2 CONH.sub.2                                                                     230-234                                 Cl    CF.sub.3                                                                             N        Br    CH.sub.2 CO.sub.2 C(CH.sub.3).sub.3               Cl    CF.sub.3                                                                             N        Br    (CH.sub.2).sub.3 CO.sub.2 CH.sub.3                Cl    CF.sub.3                                                                             N        Br                                                                                   ##STR63##                                                                              118                                     Cl    Cl     N        H     CH.sub.2 CO.sub.2 CH.sub.3                                                              102-104                                 Cl    Cl     N        H                                                                                    ##STR64##                                                                              95-98                                   Cl    CF.sub.3                                                                             CH       Cl    CH.sub.2 CO.sub.2 C(CH.sub.3).sub.3                                                     120-125                                 Cl    CF.sub.3                                                                             CH       Cl    CH.sub.2 CO.sub.2 CH.sub.3                                                              85-90                                   F     CF.sub.3                                                                             CCl      NO.sub.2                                                                            CH.sub.2 CO.sub.2 CH.sub.3                        F     CF.sub.3                                                                             CCl      NO.sub.2                                                                            CH.sub.2 CO.sub.2 C(CH.sub.3).sub.3               F     CF.sub.3                                                                             CCl      F     CH.sub.2 CO.sub.2 C(CH.sub.3).sub.3                                                     150-152                                 F     CF.sub.3                                                                             CCl      Br    CH.sub.2 CO.sub.2 CH.sub.3                                                              74-75                                   F     CF.sub.3                                                                             CCl      Br                                                                                   ##STR65##                                                                              82-88                                   H     CF.sub.3                                                                             CCl      NO.sub.2                                                                            CH.sub.2 CO.sub.2 CH.sub.3                                                              166-169                                 F     CF.sub.3                                                                             CCl      F     CH.sub.2 CO.sub.2 CH.sub.3                                                              90-95                                   ______________________________________                                    

EXAMPLE 21 Preparation of m-(2-Chloro-α,α,α-trifluoro-p-tolyl)oxy!aniline ##STR66##

A mixture of 3-aminophenol (10 g, 0.092 mol),3-chloro-4-fluorobenzotrifluoride (21.83 g, 0.11 mol) and potassiumcarbonate (15.19 g, 0.11 mol) in dimethyl sulfoxide is stirred at 80° C.for 36 hours and poured into water. The aqueous mixture is extractedwith ethyl acetate. The organic extracts are combined, dried overanhydrous magnesium sulfate and concentrated in vacuo to obtain aresidue. Column chromatography of the residue using silica gel and anethyl acetate/hexanes (1:1) solution gives the title product as an amberoil which is identified by ¹ H and ¹³ CNMR spectral analyses.

Using essentially the same procedure, but substituting3-amino-4-chlorophenol for 3-aminophenol, 2-chloro-5-(2-chloro-α,α,-trifluoro-p-tolyl)oxy!aniline is obtained.

EXAMPLE 22 Preparation of 1-{(2-Chloro-α,α,α-trifluoro-p-tolyl)oxy!phenyl}-3-methylurea ##STR67##

Methyl isocyanate (1.33 g, 0.025 mol) is added to a solution of m-(2-chloro-α,α,α-trifluoro-p-tolyl)-oxy!aniline (5.8 g, 0.02 mol) intoluene. The reaction mixture is stirred at 60° C. for 90 minutes andfiltered to obtain the title product as a white solid., mp 165°-169° C.

Using essentially the same procedure, but substituting 2-chloro-5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!aniline for m-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!aniline, 1-{2-chloro-5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!phenyl}-3-methylurea is obtained.

EXAMPLE 23 Preparation of 1-{3-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!phenyl}-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione##STR68##

N-(Chlorocarbonyl) isocyanate (1.5 g, 0.0143 mol) is added to a mixtureof 1-{ (2-chloro-α,α,α-trifluoro-p-tolyl)oxy!phenyl}-3-methylurea (4.1g, 0.0119 mol.) in toluene. The reaction mixture is stirred at 60° C.for 18 hours, cooled to room temperature and concentrated in vacuo toobtain a glass. The glass is dried in a Kugelrohr apparatus to give thetitle product as a yellow glass which is identified by ¹ H and ¹³ CNMRspectral analyses.

Using essentially the same procedure, but employing the appropriatelysubstituted 1-phenyl-3-methylurea, the following compounds are obtained:

    ______________________________________                                         ##STR69##                                                                    X        X.sub.2                                                                              X.sub.4     Y.sub.1                                                                           mp °C.                                 ______________________________________                                        Cl       CF.sub.3                                                                             H           Cl  200-204                                       Cl       CF.sub.3                                                                             F           F                                                 ______________________________________                                    

EXAMPLE 24 Preparation of 3-{2-Bromo-5-{3-chloro-5-(trifluoromethyl)-2-pyridyl!oxy}phenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-aceticacid ##STR70##

A solution of tert-butyl 3-{2-bromo-5-{3-chloro-5-(trifluoromethyl)-2-pyridyl!oxy}phenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate(7.00 g, 0.012 mol) in trifluoroacetic acid (40 mL) is refluxed for 2.5hours, cooled to room temperature and concentrated in vacuo to give thetitle product which is identified by ¹ HNMR spectral analysis.

Using essentially the same procedure, but substituting tert-butyl 3-{5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!-2-nitrophenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetatefor tertbutyl 3-{2-bromo-5-{(3-chloro-5-(trifluoromethyl)-2-pyridyl!oxy}phenyl}tetrahydro-5-methyl-22,4,(6-trioxo-s-triazine-1(2H)-acetate,3-{5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!-2-nitrophenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-aceticacid is obtained as a yellow glass.

EXAMPLE 25 Preparation of 3-{2-Bromo-5-{3-chloro-5-(tri-fluoromethyl)-2-pyridyl!oxy}phenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetylchloride ##STR71##

A solution of 3-{2-bromo-5-{3-chloro-5-(trifluoromethyl)-2-pyridyl!oxy}phenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-aceticacid (from Example 24) in thionyl chloride is refluxed for 6 hours andconcentrated in vacuo to give the title product.

EXAMPLE 26 Preparation of 2-Fluoroethyl 3-{2-bromo-5-{3-chloro-5-(trifluoromethyl)-2-pyridyl!oxy}phenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate##STR72##

A solution of 3-{2-bromo-5-{3-chloro-5-(trifluoromethyl)-2-pyridyl!oxy}phenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetylchloride (0.86 g, 1.6 mmol) in tetrahydrofuran is cooled to 0° C.,treated with 2-fluoroethanol (0.206 g, 3.2 mmol) and triethylamine (0.6mL, 4.3 mmol), stirred at room temperature overnight and diluted withethyl acetate. The organic mixture is washed sequentially with water,hydrochloric acid, sodium hydrogen carbonate solution and water, driedover anhydrous magnesium sulfate and concentrated in vacuo to obtain aresidue. Column chromatography of the residue using silica gel and a 20%ethyl acetate in petroleum ether solution gives the title product as asolid, mp 93°-95° C.

Using essentially the same procedure, but using the appropriate alcohol,the following compounds are obtained:

    ______________________________________                                         ##STR73##                                                                    R.sub.14           mp °C.                                              ______________________________________                                         ##STR74##         89-90                                                      CH.sub.2 CO.sub.2 (CH.sub.2).sub.5 CH.sub.3                                                      124-127                                                    ______________________________________                                    

EXAMPLE 27 Preparation of N-{{3-{2-Bromo-5-{3-chloro-5-(trifluoromethyl)-2-pyridyl!oxy}phenyl}-3,4,5,6-tetrahydro-5-methyl-2,4,6-trioxo-s-triazin-1(2H)-yl}acetyl}glycinemethyl ester ##STR75##

A solution of 3-{2-bromo-5-{3-chloro-5-(trifluoromethyl)-2-pyridyl!oxy}phenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetylchloride (0.60 g, 1.1 mmol) in tetrahydrofuran is cooled to 0° C.,treated with glycine methyl ester hydrochloride (0.213 g, 1.7 mmol) andtriethylamine (0.334 g, 3.3 mmol), stirred at room temperature for 2.5hours and diluted with ethyl acetate. The organic mixture is washedsequentially with water, hydrochloric acid, water, sodium hydroxidesolution, sodium hydrogen carbonate solution and water, dried overanhydrous magnesium sulfate and concentrated in vacuo to obtain aresidue. Column chromatography of the residue using silica gel and anethyl acetate/hexanes (1:5) solution affords a solid which is washedwith petroleum ether and dried to give the title product as a whitesolid which is identified by ¹ H and ¹³ CNMR spectral analyses.

Using essentially the same procedure, but substituting dimethylaminehydrochloride for glycine methyl ester hydrochloride, 3-{2-bromo-5-{3-chloro-5-(trifluoromethyl)-2-pyridyl!oxy!phenyl}tetrahydro-N,N,5-trimethyl-2,4,6-trioxo-s-triazine-1(2H)-acetamideis obtained as a white solid.

EXAMPLE 28 Preparation of 2-Bromo-5-hydroxybenzoic acid ##STR76##

A mixture of 2-bromo-5-methoxybenzoic acid (10 g, 0.043 mol) inmethylene chloride is cooled to -60° C., treated with boron tribromide(3.59 g, 0.143 mol), stirred at -60° C. for 1 hour, stirred at roomtemperature for 1 hour, cooled to -70° C., treated with additional borontribromide (3.59 g, 0.143 mol), stirred at -70° C. for 1 hour, stirredat room temperature for 1 hour and poured into water. The aqueousmixture is extracted with ethyl acetate. The organic extracts arecombined, washed with brine, dried over anhydrous sodium sulfate andconcentrated in vacuo to give the title product as a white solid whichis identified by ¹ H and ¹³ CNMR spectral analyses.

EXAMPLE 29 Preparation of 2-Bromo-5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!benzoic acid ##STR77##

A mixture of 2-bromo-5-hydroxybenzoic acid (6.55 g, 0.030 mol),5-chloro-α,α,α,3,4-pentafluorotoluene (6.93 g, 0.032 mol) and potassiumcarbonate (8.29 g, 0.060 mol) in acetonitrile is refluxed for 18 hours,treated with N,N-dimethylformamide (50 mL), refluxed overnight, cooledto room temperature and poured into water. The aqueous mixture isneutralized to pH 7 with 1N hydrochloric acid and extracted with ether.The organic extracts are combined, washed with water, dried overanhydrous sodium sulfate and concentrated in vacuo to obtain an oil. Asolution of the oil in ether is washed with-water, dried over anhydroussodium sulfate and concentrated in vacuo to give the title product as awhite solid, mp 113°-117° C.

EXAMPLE 30 Preparation of 2-Bromo-5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!benzoyl chloride ##STR78##

A mixture of 2-bromo-5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!benzoic acid (15 g, 0.035 mol)in thionyl chloride (75 mL) is heated at 60° C. for 2 hours andconcentrated in vacuo to give the title product.

Using essentially the same procedure, but substituting 5-(2-chloro-α,α,α,6-trifluoro-p-tolyl)oxy!-2-nitrobenzoic acid for2-bromo-5- (2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!benzoic acid, 5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrobenzoyl chloride isobtained.

EXAMPLE 31 Preparation of 2-Bromo-5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!benzamide ##STR79##

A solution of 2-bromo-5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!benzoyl chloride (16 g, 0.036mol) in methylene chloride is cooled to 0° C., treated dropwise with 9.2mL of a 30% ammonium hydroxide solution (0.071 mol), stirred at 0° C.for 30 minutes, stirred at room temperature overnight and poured intowater. The aqueous mixture is extracted with methylene chloride. Theorganic extracts are combined, washed sequentially with saturated sodiumhydrogen carbonate solution and brine, dried over anhydrous magnesiumsulfate and concentrated in vacuo to give the title product as a whitesolid, mp 115°-116° C.

Using essentially the same procedure, but substituting 5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrobenzoyl chloride for2-bromo-5- (2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!benzoyl chloride,5- (2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrobenzamide is obtained.

EXAMPLE 32 Preparation of 1-{2-Bromo-5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!phenyl}-3-methylurea ##STR80##

A mixture of 50% sodium hydroxide solution (0.37 g) and sodiumhypochlorite solution (3.4 mL, 5% chlorine) is added to a mixture of2-bromo-5- (2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!benzamide (2 g, 4.9mmol) in methanol at 0° C. After the addition, the reaction mixture istreated with water (10 mL), saturated with anhydrous monomethyl amine,stirred at 50° C. for 1 hour, cooled to room temperature and filtered toobtain a solid. The solid is air-dried to give the title product as awhite solid which is identified by ¹ H and ¹³ CNMR spectral analyses.

Using essentially the same procedure, but substituting 5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrobenzamide for 2-bromo-5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!benzamide, 1-{5-(2-chloro-α,α,α,-trifluoro-p-tolyl)oxy!-2-nitrophenyl}-3-methylurea isobtained as a yellow solid.

EXAMPLE 33 Preparation of 1-{2-Bromo-5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!phenyl}-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione##STR81##

A mixture of 1-{2-bromo-5-(2-chloro-(α,α,α,6-tetrafluoro-p-tolyl)oxy!phenyl}-3-methylurea (4.0 g,9.1 mmol) in toluene is treated with N-(chlorocarbonyl) isocyanate (1.2g, 11.4 mmol), stirred at 80° C. for 18 hours, cooled to roomtemperature and concentrated in vacuo to obtain a solid. A solution ofthe solid in methylene chloride is washed with brine, dried overanhydrous magnesium sulfate and concentrated in vacuo to give the titleproduct as a white solid, mp 211°-215° C.

Using essentially the same procedure, but substituting 1-{5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenyl}-3-methylurea for1-{2-bromo-5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!phenyl}-3-methylurea, 1-{5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenyl}-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trioneis obtained as a white solid.

EXAMPLE 34 Preparation of 5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenyl isocyanate##STR82##

A solution of 5- (2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrobenzamide(108 g, 0.299 mol) in methanol is cooled to 0° C., treated with asolution of 5% sodium hypochlorite solution (487 mL, 0.359 mol) and 50%sodium hydroxide solution (28.7 g, 0.359 mol) in methanol over 20minutes, and poured into brine. The aqueous mixture is extracted withmethylene chloride, adjusted to pH 5 to pH 6 with concentratedhydrochloric acid and extracted with additional methylene chloride. Theorganic extracts are combined, dried over anhydrous magnesium sulfateand concentrated in vacuo to give the title product as a yellow solid.

Using essentially the same procedure, but substituting 5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!-2-cyanobenzamide for 5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrobenzamide, 5-(2-chloro-α,αα,6-tetra-fluoro-p-tolyl)oxy!-2-cyanophenyl isocyanate isobtained

EXAMPLE 35 Preparation of N-{{5-(2-Chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenyl}carbamoyl}glycineethyl ester ##STR83##

A solution of 5- (2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenylisocyanate (107 g, 0.299) mol) in methylene chloride is cooled to 0° C.,treated with a mixture of glycine ethyl ester hydrochloride (50.1 g,0.359 mol) and triethylamine (166 mL, 1.20 mol) in methylene chlorideover 10 minutes, refluxed overnight, cooled to room temperature, washedsequentially with water and brine, dried over anhydrous magnesiumsulfate and concentrated in vacuo to obtain a solid. A solution of thesolid in methylene chloride is placed on a silica gel plug, eluted withmethylene chloride and concentrated in vacuo to give the title productas a yellow solid which is identified by ¹ H and ¹³ CNMR spectralanalyses.

Using essentially the same procedure, but substituting 5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!-2-cyanophenyl isocyanate for5- (2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenyl isocyanate,N-{{5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!-2-cyanophenyl}carbamoyl}glycineethyl ester is obtained.

EXAMPLE 36 Preparation of Ethyl 3-{5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenyl}tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate##STR84##

A mixture of N-{{5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenyl}carbamoyl}glycineethyl ester (75.0 g, 0.162 mol) and N-(chlorocarbonyl) isocyanate (35.0g, 0.332 mol) in toluene is heated at 60° C. overnight, treated withadditional N-(chlorocarbonyl) isocyanate (4.25 g), heated at 60° C. for4 hours, cooled to room temperature and filtered to obtain a solid. Thesolid is washed with petroleum ether and dried to give the title productas a white solid which is identified by ¹ H and ¹³ CNMR spectralanalyses.

Using essentially the same procedure, but substituting N-{{5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!-2-cyanophenyl}carbamoyl}glycineethyl ester for N-{{5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenyl}carbamoyl}glycineethyl ester, ethyl 3-{5-(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!-2-cyanophenyl}tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetateis obtained as a white solid.

EXAMPLE 37 Preparation of Methyl 3-{5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenyl}-tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate##STR85##

A solution of ethyl 3-{5-(2-chloro-α,α,α-trifluoro-p-tolyl)oxy!-2-nitrophenyl}tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate(16.0 g, 0.030 mol) and sulfuric acid (1.60 mL, 0.030 mol) in methanol(240 mL, 5.92 mol) is refluxed overnight, treated with sulfuric acid(0.40 mL), refluxed for 90 minutes, treated with sulfuric acid (0.80mL), refluxed for 90 minutes, treated with sulfuric acid (0.80 mL),refluxed for 1 hour, treated with sulfuric acid (0.80 mL), refluxed for90 minutes, stirred at room temperature overnight, partiallyconcentrated in vacuo and diluted with ether. The organic mixture iswashed sequentially with water and brine, dried over anhydrous magnesiumsulfate and concentrated in vacuo to give the title product as a whitesolid, mp 166°-167° C.

EXAMPLE 38 Preparation of 2-Cyano-5-hydroxybenzamide ##STR86##

A mixture of 2-cyano-5-methoxybenzamide (5.2 g, 0.027 mol) in methylenechloride is cooled to 0° C., treated dropwise with boron tribromide (54mL of a 1M solution in methylene chloride), stirred at 0° C. for 30minutes, stirred at room temperature for 1. hour, refluxed for 4 hours,cooled to 0° C., treated with additional boron tribromide (54 mL of a 1Msolution in methylene chloride), refluxed for 17 hours, cooled to roomtemperature and diluted with water. The aqueous mixture is filtered toobtain a solid which is washed sequentially with water and ether anddried to give the title product as a beige solid, mp 268°-270° C.

EXAMPLE 39 Preparation of 5-(2-Chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy!-2-cyanobenzamide ##STR87##

A mixture of 5-chloro-α,α,α,3,4-pentafluorotoluene (2.56 g, 0.0118 mol),2-cyano-5-hydroxybenzamide (1.60 g, 0.0099 mol) and potassium carbonate(1.64 g, 0.0119 mol) in N,N-dimethylformamide is stirred at 80° C. for15 hours, cooled to room temperature and poured into an ice-watermixture. The aqueous mixture is filtered to obtain a solid which iswashed sequentially with water and hexanes and dried to give the titleproduct as a yellow solid, mp 174°-175° C.

EXAMPLE 40 Postemergence Herbicidal Evaluation of Test Compounds

The postemergence herbicidal activity of the compounds of the presentinvention is demonstrated by the following tests, wherein a variety ofdicotyledonous and monocotyledonous plants are treated with testcompounds, dispersed in aqueous acetone mixtures. In the tests, seedlingplants are grown in jiffy flats for about two weeks. The test compoundsare dispersed in 50/50 acetone/water mixtures containing 0.5% TWEEN®20,a polyoxyethylene sorbitan monolaurate surfactant of Atlas ChemicalIndustries, in sufficient quantities to provide the equivalent of about0.125 kg to 0.500 kg per hectare of active compound when applied to theplants through a spray nozzle operating at 40 psi for a predeterminedtime. After spraying, the plants are placed on greenhouse benches andare cared for in the usual manner, commensurate with conventionalgreenhouse practices. From four to five weeks after treatment, theseedling plants are examined and rated according to the rating systemset forth below. Data obtained are reported in Table I below. Where morethan one test is involved for a given compound, the data are averaged.

Plant species employed in these evaluations are reported by headerabbreviation, common name and scientific name.

Compounds employed in this postemergence herbicidal evaluation and inthe preemergence evaluation in the following example are given acompound number and identified by name. Data in Table I are reported bycompound number.

Herbicide Rating Scale

Results of herbicide evaluation are expressed on a rating scale (0-9).The scale is based upon a visual observation of plant stand, vigor,malformation, size, chlorosis and overall plant appearance as comparedwith a control.

    ______________________________________                                                                 % Control                                            Rating   Meaning         Compared to Check                                    ______________________________________                                        9        Complete kill   100                                                  8        Approaching Complete Kill                                                                     91-99                                                7        Good Herbicidal Effect                                                                        80-90                                                6        Herbicidal Effect                                                                             65-79                                                5        Definite Injury 45-64                                                4        Injury          30-44                                                3        Moderate Effect 16-29                                                2        Slight Effect    6-15                                                1        Trace Effect    1-5                                                  0        No Effect       0                                                    --       No Evaluation                                                        ______________________________________                                    

    ______________________________________                                        PLANT SPECIES EMPLOYED IN HERBICIDAL EVALUATIONS                              Header                                                                        Abb.    Common Name  Scientific Name                                          ______________________________________                                        ABUTH   Velvetleaf   ABUTILON THEOPHRASTI,                                                         MEDIC.                                                   AMBEL   Ragweed, Common                                                                            AMBROSIA ARTEMISII-                                                           FOLIA, L.                                                CASOB   Sicklepod    CASSIA OBTUSIFOLIA, L.                                   CHEAL   Lambsquarters,                                                                             CHENOPODIUM ALBUM, L.                                            Common                                                                IPOSS   Morningglory spp.                                                                          IPOMOEA SPP.                                             GALAP   Galium       GALIUM APARINE                                           ECHCG   Barnyardgrass                                                                              ECHINOCHLOA CRUS-GALLI,                                                       (L) BEAU                                                 SETVI   Foxtail, Green                                                                             SETARIA VIRIDIS,                                                              (L) BEAU                                                 GLXMAW  Soybean, Williams                                                                          GLYCINE MAX(L)                                                                MERR. CV. WILLIAMS                                       ORYSAT  Rice, Tebonnet                                                                             ORYZA SATIVA,                                                                 L. TEBONNET                                              TRZAWO  Wheat, Winter,                                                                             TRITICUM                                                         CV. APOLLO   AESTIVUM, CV. APOLLO                                     ZEAMX   Corn, Field  ZEA MAYS L.                                              ______________________________________                                    

    ______________________________________                                        COMPOUNDS EVALUATED AS HERBICIDAL AGENTS                                      Compound                                                                      Number                                                                        ______________________________________                                        1           Methyl 3-{2-bromo-5- (2-chloro-α,α,α,6-                     tetrafluoro-p-tolyl)oxy!phenyl}tetrahydro-                                    α,5-dimethyl-2,4,6-trioxo-s-triazine-1(2H)-                             acetate                                                           2           Methyl 3-{2-bromo-5- (2-chloro-α,α,α,6-                     tetrafluoro-p-tolyl)oxy!phenyl}tetrahydro-5-                                  methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate                      3           Methyl 3-{5- (2-chloro-α,α,α-trifluoro-p-                   tolyl)oxy!-2-nitrophenyl}tetrahydro-5-                                        methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate                      4           Methyl 3-{5- (2-chloro-α,α,α,6-tetrafluoro-                 4                                                                             p-tolyl)oxy!-2-fluorophenyl}tetrahydro-5-                                     methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate                      5           Ethyl 3-{5- (2-chloro-α,α,α-trifluoro-p-                    tolyl)oxy!-2-nitrophenyl}tetrahydro-2,4,6-                                    trioxo-s-triazine-1(2H)-acetate                                   6           1-Ethyl methyl 5-{5- (2-chloro-α,α,α-tri-                   fluoro-p-tolyl)oxy!-2-nitrophenyl}dihydro-                                    2,4,6-trioxo-s-triazine-1,3(2H,4H)-diacetate                      7           Ethyl 3-{5- (2-chloro-α,α,α-trifluoro-p-                    tolyl)oxy!-2-nitrophenyl}tetrahydro-2,4,6-                                    trioxo-5-(2-propynyl)-s-triazine-1(2H)-                                       acetate                                                           8           Methyl 3-{5- (2-chloro-α,α,α-trifluoro-p-                   tolyl)oxy!-2-nitrophenyl}tetrahydro-2,4,6-                                    trioxo-s-triazine-1(2H)-acetate                                   9           Ethyl 3-{5- (2-chloro-α,α,α-trifluoro-p-                    tolyl)oxy!-2-nitrophenyl}tetrahydro-5-                                        methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate                      10          Ethyl 3-{5- (2-chloro-α,α,α,6-tetrafluoro-p-                1                                                                             tolyl)oxy!-2-cyanophenyl}tetrahydro-2,4,6-                                    trioxo-s-triazine-1(2H)-acetate                                   11          Ethyl 3-{5- (2-chloro-α,α,α,6-tetrafluoro-p-                .                                                                             tolyl)oxy!-2-cyanophenyl}tetrahydro-5-                                        methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate                      12          1-Ethyl methyl 5-{5- (2-chloro-α,α,α,6-                     tetrafluoro-p-tolyl)oxy!-2-cyanophenyl}-                                      dihydro-2,4,6-trioxo-s-triazine-1,3(2H,4H)-                                   diacetate                                                         13          Ethyl 3-allyl-5-{5- (2-chloro-α,α,α-tri-                    fluoro-p-tolyl)oxy!-2-nitrophenyl}tetra-                                      hydro-2,4,6-trioxo-s-triazine-1(2H)-acetate                       14          Methyl 3- 5-(2,4-dichlorophenoxy)-2-                                          nitrophenyl!tetrahydro-2,4,6-trioxo-s-                                        triazine-1(2H)-acetate                                            15          3-{5- (2-Chloro-α,α,α,6-tetrafluoro-p-                      tolyl)oxy!-2-nitrophenyl}tetrahydro-5-                                        methyl-2,4,6-trioxo-s-triazine-1(2H)-acetic                                   acid                                                              16          Methyl 3-{5- (2-chloro-α,α,α,6-tetrafluoro-                 8                                                                             p-tolyl)oxy!-2-nitrophenyl}tetrahydro-5-                                      methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate                      17          Tert-butyl 3-{5- (2-chloro-α,α,α,6-tetra-                   fluoro-p-tolyl)oxy!-2-nitrophenyl}tetra-                                      hydro-5-methyl-2,4,6-trioxo-s-triazine-                                       1(2H)-acetate                                                     18          Methyl 3- 5-(2,4-dichlorophenoxy)-2-                                          nitrophenyl!tetrahydro-5-methyl-2,4,6-                                        trioxo-s-trizine-1(2H)-acetate                                    19          Dimethyl 5- 5-(2,4-dichlorophenoxy)-2-nitro-                                  phenyl!dihydro-2,4,6-trioxo-s-trizine-1,3-                                    (2H,4H)-diacetate                                                 20          Methyl 3-{5- (2,4-dichloro-m-tolyl)oxy!-2-                                    nitrophenyl}tetrahydro-5-methyl-2,4,6-                                        trioxo-s-triazine-1(2H)-acetate                                   21          Methyl tetrahydro-3-methyl-5-{2-nitro-5-                                       (α,α,α,4-tetrafluoro-o-tolyl)oxy!phenyl-                   2,4,6-trioxo-s-triazine-1(2H)-acetate                             22          Methyl 3- 5-(2,3-dichlorophenoxy)-2-                                          nitrophenyl!tetrahydro-5-methyl-2,4,6-                                        trioxo-s-triazine-1(2H)-acetate                                   23          Methyl 3- 5-(4-chloro-2-fluorophenoxy)-2-                                     nitrophenyl!tetrahydro-5-methyl-2,4,6-                                        trioxo-s-triazine-1(2H)-acetate                                   24          Methyl 3- 5-(2-fluoro-4-nitrophenoxy)-2-                                      nitrophenyl!tetrahydro-5-methyl-2,4,6-                                        trioxo-s-triazine-1(2H)-acetate                                   25          Methyl 3- 2-nitro-5-(2,3,5-trichloro-                                         phenoxy)phenyl!tetrahydro-5-methyl-2,4,6-                                     trioxo-s-triazine-1(2H)-acetate                                   26          Methyl 3- 2-nitro-5-(2,3,4-trichlorophen-                                     oxy)phenyl!tetrahydro-5-methyl-2,4,6-tri-                                     oxo-s-triazine-1(2H)-acetate                                      27          Methyl tetrahydro-3-methyl-5- 2-nitro-5-                                      (2,3,4-trifluorophenoxy)phenyl!-2,4,6-                                        trioxo-s-triazine-1(2H)-acetate                                   28          Methyl 3-{2- (2-chloro-α,α,α,-trifluoro-p-                  tolyl)oxy!phenyl}tetrahydro-5-methyl-2,4,6-                                   trioxo-s-triazine-1(2H)-acetate                                   29          Methyl 3- 5-(2,4-dichloro-5-methoxyphenoxy)-                                  2-nitrophenyl!tetrahydro-5-methyl-2,4,6-                                      trioxo-s-triazine-1(2H)-acetate                                   30          Methyl tetrahydro-3-methyl-5- 2-nitro-5-                                      (2,4,5-trifluorophenoxy)phenyl-2,4,6-trioxo-                                  s-triazine-1(2H)-acetate                                          31          Methyl tetrahydro-3-methyl-5- 2-nitro-5-                                      (2,4,5-trichlorophenoxy)phenyl!-2,4,6-                                        trioxo-s-triazine-1(2H)-acetate                                   32          Methyl 3- 5-(p-cyanophenoxy)-2-nitrophenyl!-                                  tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-                                  1(2H)-acetate                                                     33          Methyl tetrahydro-3-methyl-5- 2-nitro-5-                                      (2,4,6-trichlorophenoxy)phenyl!-2,4,6-                                        trioxo-s-triazine-1(2H)-acetate                                   34          Methyl 3-{5- 2-chloro-4-(methylthio)-                                         phenoxy!-2-nitrophenyl}tetrahydro-5-methyl-                                   2,4,6-trioxo-s-triazine-1(2H)-acetate                             35          Methyl 3- 5-(3,5-dichlorophenoxy)-2-                                          nitrophenyl!tetrahydro-5-methyl-2,4,6-                                        trioxo-s-triazine-1(2H)-acetate                                   36          Methyl 3-{ 2-chloro-4-(methylsulfinyl)-                                       phenoxy!-2-nitrophenyl}tetrahydro-5-methyl-                                   2,4,6-trioxo-s-triazine-1(2H)-acetate                             37          Methyl 3- 5-(2,6-dichlorophenoxy)-2-                                          nitrophenyl!tetrahydro-5-methyl-2,4,6-                                        trioxo-s-triazine-1(2H)-acetate                                   38          Methyl tetrahydro-3-methyl-5- 2-nitro-5-(2-                                   pyridyloxy)phenyl!-2,4,6-trioxo-s-triazine-                                   1(2H)-acetate                                                     39          Methyl 3-{ 2-chloro-5-(2-chloro-α,α,α-                      trifluoro-p-tolyl)oxy!phenyl}tetrahydro-5-                                    methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate                      40          Tert-butyl 3-{ 2-chloro-5-(2-chloro-α,α,α-                  trifluoro-p-tolyl)oxy!phenyl}tetrahydro-5-                                    methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate                      41          Tert-butyl 3-{ 5-(2-chloro-α,α,α,6-tetra-                   fluoro-p-tolyl)oxy!-2-fluorophenyl}tetra-                                     hydro-5-methyl-2,4,6-trioxo-s-triazine-                                       1(2H)-acetate                                                     42          3-{ 2-Bromo-5-{ 3-chloro-5-(trifluoro-                                        methyl)-2-pyridyl!oxy}phenyl}tetrahydro-5-                                    methyl-2,4,6-trioxo-s-triazine-1(2H)-                                         acetamide                                                         43          Methyl 3- 2-bromo-5-(2,4-dichlorophenoxy)-                                    phenyl!tetrahydro-5-methyl-2,4,6-trioxo-s-                                    triazine-1(2H)-acetate                                            44          Isopropyl 3-{ 2-bromo-5-{ 3-chloro-5-                                         (trifluoromethyl)-2-pyridyl!oxy}phenyl}-                                      tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-                                  1(2H)-acetate                                                     45          Methyl 3-{ 2-bromo-5-{ 3-chloro-5-(tri-                                       fluoromethyl)-2-pyridyl!oxy}phenyl}tetra-                                     hydro-5-methyl-2,4,6-trioxo-s-triazine-                                       1(2H)-acetate                                                     46          3-{5- (2-Chloro-α,α,α-trifluoro-p-tolyl)-                   oxy!phenyl}tetrahydro-5-methyl-2,4,6-trioxo-                                  s-triazine-1(2H)-acetamide                                        ______________________________________                                    

                                      TABLE I                                     __________________________________________________________________________    Postemergence Herbicidal Evaluations Of Test Compounds                        Com-                                                                          pound                                                                             Rate                                                                      Number                                                                            (kp/ha)                                                                           ABUTH                                                                              AMBEL                                                                              CASOB                                                                             CHEAL                                                                             IPOSS                                                                             GALAP                                                                             ECHCG                                                                             SETVI                                                                             GLXMAW                                                                              ORYSAT                                                                             TRZAWO                                                                             ZEAMX               __________________________________________________________________________     1  0.500                                                                             9.0  6.0  --  9.0 9.0 --  2.0 4.0 5.0   --   --   3.0                     0.250                                                                             9.0  5.0  --  9.0 9.0 --  2.0 2.0 6.0   --   --   2.0                     0.125                                                                             9.0  3.0  --  9.0 8.0 --  1.0 0.0 4.0   --   --   1.0                  2  0.500                                                                             9.0  8.0  9.0 8.5 9.0 9.0 9.0 9.0 8.3   7.5  8.5  8.3                     0.250                                                                             9.0  7.5  9.0 8.5 9.0 9.0 9.0 9.0 8.0   7.0  8.0  8.3                     0.125                                                                             9.0  7.3  9.0 8.7 8.7 9.0 6.7 9.0 7.2   6.3  7.5  8.4                  3  0.500                                                                             8.6  9.0  8.8 8.2 8.8 9.0 8.8 8.6 7.3   7.1  8.1  7.5                     0.250                                                                             9.0  9.0  8.5 7.5 9.0 8.7 8.6 8.5 6.5   6.7  7.8  7.2                     0.125                                                                             9.0  8.8  9.0 7.4 8.8 8.8 7.3 7.6 6.2   5.8  7.4  6.1                  4  0.500                                                                             9.0  8.8  8.8 9.0 9.0 9.0 9.0 9.0 7.8   7.0  8.6  8.8                     0.250                                                                             9.0  8.8  9.0 9.0 9.0 8.8 8.9 9.0 7.1   6.3  8.2  8.8                     0.125                                                                             9.0  8.3  9.0 8.8 9.0 8.7 8.0 9.0 6.2   5.6  8.0  8.8                  5  0.500                                                                             9.0  9.0  8.5 8.0 9.0 9.0 6.0 6.5 5.8   4.8  6.0  6.0                     0.250                                                                             9.0  9.0  8.0 8.0 9.0 9.0 5.5 4.0 5.5   4.8  5.5  4.5                     0.125                                                                             9.0  8.5  6.5 8.0 9.0 7.5 4.0 4.5 4.8   4.0  5.0  4.5                  6  0.500                                                                             9.0  9.0  6.5 4.5 8.0 8.0 4.5 2.0 4.5   4.3  5.3  4.5                     0.250                                                                             9.0  8.5  8.0 3.0 8.0 7.0 4.5 2.0 4.8   4.3  5.0  4.5                     0.125                                                                             9.0  8.0  7.0 1.5 7.0 6.0 3.5 0.5 4.0   3.8  4.3  4.0                  7  0.500                                                                             7.0  7.0  7.0 4.0 9.0 4.0 6.0 3.0 4.5   5.5  5.5  5.0                     0.250                                                                             9.0  8.0  7.0 3.0 8.0 6.0 6.0 0.0 4.0   5.0  5.0  4.5                     0.125                                                                             7.0  6.0  6.0 3.0 9.0 3.0 8.0 0.0 4.5   5.0  4.5  4.5                  8  0.500                                                                             9.0  9.0  9.0 9.0 9.0 9.0 7.0 6.0 5.5   6.6  6.0  6.5                     0.250                                                                             9.0  9.0  9.0 9.0 9.0 9.0 3.0 3.0 5.0   5.5  5.5  6.0                     0.125                                                                             9.0  9.0  7.0 9.0 9.0 8.0 0.0 0.0 5.0   5.0  4.5  5.0                  9  0.500                                                                             9.0  9.0  9.0 9.0 9.0 9.0 6.0 9.0 5.5   6 5  8 5  6 5                     0.250                                                                             9.0  9.0  9.0 9.0 9.0 8.0 5.0 7.0 4.5   4.5  7.5  5.0                     0.125                                                                             9.0  9.0  9.0 9.0 9.0 8.0 4.0 8.0 4.5   4.5  7.5  4.5                 10  0.500                                                                             9.0  9.0  7.0 9.0 9.0 7.0 3.0 3.0 6.5   4.5  5.5  4.5                     0.250                                                                             9.0  8.0  8.0 9.0 8.0 7.0 2.0 0.0 5.0   4.0  3.0  3.5                     0.125                                                                             9.0  9.0  5.0 9.0 9.0 5.0 2.0 2.0 4.5   3.5  3.0  3.5                 11  0.500                                                                             9.0  9.0  9.0 9.0 9.0 8.0 8.0 9.0 6.0   5.0  7.0  9.0                     0.250                                                                             9.0  9.0  9.0 9.0 9.0 8.0 7.0 9.0 5.0   5.0  7.5  9.0                     0.125                                                                             9.0  9.0  9.0 9.0 9.0 5.0 3.0 9.0 4.5   4.5  6.0  8.0                 12  0.500                                                                             9.0  8.0  9.0 9.0 9.0 7.0 3.0 7.0 4.0   5.0  5.0  4.5                     0.250                                                                             7.0  6.0  8.0 9.0 6.0 7.0 3.0 2.0 5.5   4.0  4.5  4.5                     0.125                                                                             8.0  6.0  7.0 9.0 9.0 5.0 4.0 0.0 4.0   3.5  4.5  4.0                 13  0.500                                                                             9.0  9.0  7.0 9.0 6.0 9.0 3.0 2.0 5.5   3.5  5.5  5.0                     0.250                                                                             9.0  9.0  9.0 7.0 6.0 8.0 3.0 0.0 5.5   4.0  5.0  4.0                     0.125                                                                             8.0  8.0  6.0 5.0 5.0 6.0 0.0 0.0 4.5   3.0  4.5  4.0                 14  0.500                                                                             9.0  9.0  9.0 9.0 8.0 7.0 4.0 4.0 5.5   5.5  6.5  6.0                     0.250                                                                             9.0  9.0  9.0 9.0 7.0 5.0 3.0 3.0 5.5   6.0  5.5  5.5                     0.125                                                                             8.0  8.0  8.0 8.0 7.0 4.0 3.0 3.0 5.0   5.5  5.5  5.0                 15  0.500                                                                             9.0  9.0  9.0 5.0 9.0 9.0 8.0 4.0 5.7   8.5  9.0  7.0                     0.250                                                                             9.0  9.0  9.0 4.0 9.0 8.5 9.0 2.5 5.7   8.5  9.0  6.7                     0.125                                                                             9.0  9.0  9.0 0.0 8.0 8.0 6.0 1.0 4.7   6.0  8.3  4.3                 16  0.500                                                                             9.0  9.0  9.0 9.0 9.0 9.0 8.7 3.7 6.2   7.8  8.4  6.4                     0.250                                                                             9.0  9.0  9.0 7.5 9.0 9.0 7.0 3.0 6.4   7.3  8.4  5.0                     0.125                                                                             9.0  9.0  9.0 6.5 9.0 9.0 3.7 1.3 5.6   5.8  8.4  4.2                 17  0.500                                                                             9.0  9.0  8.0 5.0 8.0 9.0 2.5 2.0 4.0   3.0  3.7  3.3                     0.250                                                                             9.0  9.0  9.0 4.0 9.0 8.0 2.0 1.0 3.3   4.0  3.7  3.0                     0.125                                                                             9.0  8.5  6.5 2.0 9.0 7.5 0.5 0.5 3.3   3.5  3.0  2.7                 18  0.500                                                                             9.0  8.0  9.0 9.0 9.0 9.0 9.0 9.0 5.0   5.0  7.5  8.0                     0.250                                                                             9.0  7.0  9.0 9.0 9.0 9.0 8.0 9.0 5.0   5.0  8.0  8.0                     0.125                                                                             9.0  8.0  9.0 9.0 9.0 9.0 6.0 8.0 5.5   3.5  7.5  7.0                 19  0.500                                                                             9.0  9.0  9.0 9.0 8.0 9.0 4.0 5.0 5.5   4.0  5.5  4.0                     0.250                                                                             9.0  9.0  9.0 9.0 9.0 9.0 3.0 5.0 4.5   5.0  5.0  3.5                     0.125                                                                             9.0  6.0  9.0 7.0 8.0 9.0 3.0 3.0 4.0   4.0  4.5  3.5                 20  0.500                                                                             9.0  7.0  9.0 7.0 9.0 6.0 3.0 5.0 5.5   4.5  5.0  5.5                     0.250                                                                             9.0  8.0  8.0 9.0 9.0 3.0 2.0 3.0 5.5   3.5  5.0  5.0                     0.125                                                                             9.0  5.0  8.0 8.0 9.0 6.0 0.0 2.0 4.5   4.0  4.0  4.5                 21  0.500                                                                             9.0  4.0  4.0 9.0 6.0 4.5 9.0 9.0 4.0   4.5  8.0  8.5                     0.250                                                                             9.0  3.0  5.0 5.0 9.0 6.0 8.0 9.0 4.0   4.5  7.5  8.0                     0.125                                                                             7.0  2.0  4.0 4.0 8.0 3.0 6.0 7.0 4.0   3.5  7.0  7.5                 22  0.500                                                                             8.0  3.0  3.5 5.0 4.0 3.0 5.0 4.0 4.0   3.5  5.0  3.5                     0.250                                                                             8.0  3.0  6.0 4.0 7.0 6.0 2.0 2.0 4.0   4.0  5.0  3.5                     0.125                                                                             7.0  0.0  3.0 2.0 4.0 6.0 0.0 0.0 3.0   3.5  4.0  3.0                 23  0.500                                                                             9.0  8.0  4.0 8.0 9.0 4.5 9.0 8.0 6.0   5.0  8.5  6.0                     0.250                                                                             9.0  6.0  9.0 6.0 9.0 6.0 6.0 5.0 4.5   4.5  7.5  5.5                     0.125                                                                             8.0  5.0  6.0 6.0 8.0 9.0 5.0 3.0 4.5   4.0  7.5  4.5                 24  0.500                                                                             3.0  4.0  1.5 2.0 4.0 2.0 0.0 0.0 1.5   1.5  2.0  2.0                     0.250                                                                             2.0  4.0  2.0 0.0 4.0 2.0 0.0 0.0 1.5   1.5  2.0  1.5                     0.125                                                                             0.0  1.0  0.0 0.0 2.0 2.0 0.0 0.0 0.5   1.0  1.0  1.5                 25  0.500                                                                             0.0  0.0  0.0 0.0 0.0 0.0 0.0 0.0 0.0   1.0  0.5  1.0                     0.250                                                                             0.0  0.0  0.0 0.0 0.0 0.0 0.0 0.0 0.0   0.5  0.5  1.0                     0.125                                                                             0.0  0.0  0.0 0.0 0.0 0.0 0.0 0.0 0.0   0.0  0.0  0.0                 26  0.500                                                                             9.0  7.0  9.0 9.0 9.0 7.0 4.0 3.0 5.0   5.0  5.0  5.5                     0.250                                                                             8.0  7.0  3.5 8.0 7.0 4.0 2.0 0.0 5.0   4.5  5.0  4.0                     0.125                                                                             6.0  6.0  7.0 6.0 8.0 5.0 0.0 0.0 4.0   3.5  4.0  3.5                 27  0.500                                                                             9.0  5.0  3.0 6.0 7.0 4.5 9.0 4.0 3.5   4.5  5.5  4.5                     0.250                                                                             8.0  5.0  5.0 5.0 6.0 6.0 5.0 2.0 3.0   4.0  5.0  4.0                     0.125                                                                             7.0  2.0  2.0 3.0 4.0 6.0 2.0 0.0 2.5   3.5  3.5  3.5                 28  0.500                                                                             9.0  7.0  6.5 9.0 9.0 4.5 2.0 4.0 5.0   3.0  2.0  4.5                     0.250                                                                             7.0  6.0  6.0 8.0 8.0 5.0 0.0 2.0 4.5   2.5  2.0  4.0                     0.125                                                                             6.0  4.0  5.0 6.0 6.0 4.0 0.0 1.0 3.5   2.0  2.0  2.5                 29  0.500                                                                             7.0  8.0  5.5 9.0 6.0 2.0 1.0 2.0 4.5   2.5  3.0  4.5                     0.250                                                                             7.0  7.0  8.0 7.0 5.0 3.0 0.0 1.0 4.5   2.0  3.0  3.5                     0.125                                                                             5.0  6.0  7.0 6.0 5.0 0.0 0.0 0.0 3.5   1.5  2.0  3.5                 30  0.500                                                                             5.0  6.0  4.5 5.0 5.0 5.0 1.0 1.0 4.0   3.0  4.5  4.5                     0.250                                                                             5.0  5.0  4.0 5.0 4.0 6.0 1.0 2.0 4.0   3.0  4.0  3.0                     0.125                                                                             3.0  4.0  5.0 4.0 4.0 3.0 0.0 0.0 4.5   3.0  3.5  3.0                 31  0.500                                                                             7.0  8.0  5.5 7.0 6.0 2.5 0.0 0.0 4.5   4.0  5.5  4.0                     0.250                                                                             7.0  7.0  8.0 7.0 6.0 4.0 2.0 2.0 4.0   4.0  5.0  4.0                     0.125                                                                             5.0  7.0  9.0 7.0 5.0 4.0 0.0 1.0 3.5   3.0  3.5  3.5                 32  0.500                                                                             0.0  0.0  0.0 2.0 0.0 0.0 0.0 0.0 3.0   1.5  1.5  2.0                     0.250                                                                             0.0  0.0  0.0 0.0 0.0 0.0 0.0 0.0 2.5   1.0  1.5  1.5                     0.125                                                                             0.0  0.0  0.0 0.0 0.0 0.0 0.0 0.0 2.0   1.0  1.0  1.5                 33  0.500                                                                             9.0  9.0  9.0 9.0 9.0 9.0 4.0 5.0 6.0   6.5  7.0  5.0                     0.250                                                                             9.0  8.0  9.0 9.0 8.0 9.0 3.0 4.0 5.5   5.5  6.5  5.0                     0.125                                                                             8.0  8.0  7.5 8.0 7.0 5.5 2.0 2.0 4.5   5.5  6.0  4.5                 34  0.500                                                                             5.0  2.0  3.0 4.0 4.0 3.0 0.0 0.0 3.5   2.5  2.0  4.0                     0.250                                                                             3.0  2.0  2.0 2.0 5.0 0.0 0.0 0.0 2.5   2.0  2.0  3.5                     0.125                                                                             2.0  2.0  0.0 3.0 3.0 0.0 0.0 0.0 2.0   1.5  2.0  3.5                 35  0.500                                                                             0.0  0.0  0.0 0.0 2.0 0.0 0.0 0.0 0.5   0.5  0.0  1.0                     0.250                                                                             0.0  0.0  0.0 0.0 1.0 0.0 0.0 0.0 1.0   0.5  0.0  1.0                     0.125                                                                             0.0  0.0  0.0 0.0 1.0 0.0 0.0 0.0 0.5   0.0  0.0  1.0                 36  0.500                                                                             8.0  8.0  5.0 8.0 8.0 4.0 4.0 3.0 5.0   3.5  3.0  4.0                     0.250                                                                             7.0  7.0  5.0 8.0 6.0 8.0 2.0 2.0 5.0   3.0  3.0  3.5                     0.125                                                                             7.0  6.0  6.0 8.0 9.0 6.0 0.0 0.0 5.0   3.0  2.5  4.0                 37  0.500                                                                             8.0  6.0  2.5 6.0 5.0 3.0 4.0 3.0 5.0   3.5  5.5  4.0                     0.250                                                                             6.0  4.0  5.0 5.0 3.0 5.0 2.0 2.0 4.5   2.0  4.0  2.0                     0.125                                                                             5.0  4.0  2.0 3.0 6.0 6.0 2.0 0.0 3.5   1.5  3.5  1.5                 38  0.500                                                                             0.0  0.0  0.0 0.0 0.0 0.0 0.0 0.0 0.5   0.0  0.0  0.0                 39  0.500                                                                             9.0  9.0  9.0 9.0 9.0 9.0 8.0 9.0 7.0   4.5  5.5  8.5                     0.250                                                                             9.0  9.0  9.0 9.0 9.0 9.0 7.5 8.0 6.3   4.8  6.0  8.0                     0.125                                                                             9.0  8.5  9.0 9.0 9.0 8.0 4.5 4.5 5.5   4.3  4.8  6.5                 40  0.500                                                                             9.0  7.5  9.0 9.0 9.0 7.0 1.0 3.5 5.3   4.8  4.5  4.8                     0.250                                                                             6.5  7.0  7.5 7.0 7.5 7.0 2.5 2.0 4.0   3.3  2.3  4.0                     0.125                                                                             7.0  4.5  5.5 5.0 7.5 5.5 0.0 1.0 3.8   1.8  2.3  3.3                 41  0.500                                                                             6.0  4.0  3.0 4.0 5.0 4.0 3.0 4.0 4.0   3.0  3.5  3.5                     0.250                                                                             6.5  6.0  5.5 6.0 6.0 3.0 2.5 3.0 4.0   3.5  3.3  4.8                     0.125                                                                             6.0  4.0  3.0 5.0 5.0 2.5 0.0 0.0 3.5   2.5  2.3  3.3                 42  0.500                                                                             7.0  4.5  3.7 6.5 6.5 2.0 1.5 1.0 4.3   3.0  2.0  3.0                     0.250                                                                             4.0  3.0  4.0 6.5 4.0 3.0 1.0 1.0 4.3   2.3  1.3  2.8                     0.125                                                                             2.0  2.0  2.5 3.5 3.0 2.0 0.5 1.0 3.5   1.8  1.3  2.3                 43  0.500                                                                             9.0  6.5  9.0 9.0 7.0 5.0 7.5 8.0 6.0   5.0  7.0  8.3                     0.250                                                                             8.5  6.5  8.0 8.5 9.0 4.0 4.5 4.5 5.0   4.8  5.3  6.5                     0.125                                                                             5.5  5.5  7.5 8.5 6.5 3.5 3.0 2.5 4.5   4.0  4.8  4.8                 44  0.500                                                                             9.0  9.0  9.0 9.0 9.0 5.0 9.0 9.0 5.5   6.0  9.0  9.0                     0.250                                                                             9.0  9.0  9.0 9.0 9.0 2.0 9.0 9.0 5.5   5.5  9.0  9.0                     0.125                                                                             2.0  5.0  9.0 9.0 9.0 0.0 3.0 9.0 5.0   4.5  7.5  6.5                 45  0.500                                                                             9.0  9.0  9.0 9.0 9.0 9.0 9.0 9.0 7.5   6.5  9.0  9.0                     0.250                                                                             9.0  9.0  9.0 9.0 9.0 3.0 9.0 9.0 7.5   5.5  9.0  9.0                     0.125                                                                             9.0  9.0  9.0 9.0 9.0 7.0 7.0 9.0 7.0   5.0  9.0  9.0                 46  0.500                                                                             3.0  0.0  0.0 2.0 4.0 1.0 0.0 0.0 4.5   2.5  1.0  1.0                     0.250                                                                             2.0  0.0  0.0 7.0 3.0 3.0 0.0 0.0 3.5   2.5  1.0  1.0                     0.125                                                                             0.0  0.0  0.0 4.0 3.0 0.0 0.0 0.0 2.0   1.5  0.5  0.5                 __________________________________________________________________________

EXAMPLE 41 Preemergence Herbicidal Evaluation of Test Compounds

The preemergence herbicidal activity of the test compounds of thepresent invention is exemplified by the following tests in which theseeds of a variety of monocotyledonous and dicotyledonous plants areseparately mixed with potting soil and planted on top of approximatelyone inch of soil in separate pint cups. After planting, the cups aresprayed with the selected aqueous acetone solution containing testcompound in sufficient quantity to provide the equivalent of about 0.125to 0.50 kg per hectare of test compound per cup. The treated cups arethen placed on greenhouse benches, watered and cared for in accordancewith conventional greenhouse procedures. From four to five weeks aftertreatment, the tests are terminated and each cup is examined and ratedaccording to the rating system provided in Example 40.

The data obtained are reported in Table II below. The compoundsevaluated are reported by compound number given in Example 40.

                                      TABLE II                                    __________________________________________________________________________    Preemergence Herbicidal Evaluations Of Test Compounds                         Com-                                                                          pound                                                                             Rate                                                                      Number                                                                            (kg/ha)                                                                           ABUTH                                                                              AMBEL                                                                              CASOB                                                                             CHEAL                                                                             IPOSS                                                                             GALAP                                                                             ECHCG                                                                             SETVI                                                                             GLXMAW                                                                              ORYSAT                                                                             TRZAWO                                                                             ZEAMX               __________________________________________________________________________     1  0.500                                                                             9.0  0.0  --  9.0 6.0 --  3.0 9.0 3.0   --   1.0  4.0                     0.250                                                                             6.0  0.0  --  9.0 4.0 --  2.0 5.0 2.0   --   1.0  4.0                     0.125                                                                             0.0  0.0  --  9.0 0.0 --  2.0 2.0 2.0   --   0.0  0.0                  2  0.500                                                                             9.0  8.5  9.0 9.0 9.0 9.0 8.5 9.0 8.5   8.0  5.0  6.5                     0.250                                                                             9.0  7.0  9.0 9.0 9.0 9.0 5.5 9.0 6.5   8.0  5.0  5.5                     0.125                                                                             6.0  3.7  9.0 9.0 8.0 9.0 5.0 8.3 3.7   4.5  4.0  4.0                  3  0.500                                                                             6.8  7.5  6.0 9.0 9.0 9.0 7.0 9.0 3.8   7.5  3.0  2.8                     0.250                                                                             4.6  8.6  7.6 9.0 5.7 8.4 4.8 7.6 3.6   6.7  2.6  3.2                     0.125                                                                             3.3  6.3  6.0 9.0 4.8 7.3 3.0 6.5 2.3   5.6  2.3  1.8                  4  0.500                                                                             9.0  7.3  7.3 9.0 8.0 9.0 6.8 9.0 5.3   5.8  2.0  5.0                     0.250                                                                             8.0  5.8  6.8 9.0 7.0 9.0 4.4 8.5 2.0   3.4  1.5  2.3                     0.125                                                                             5.8  2.8  2.8 9.0 4.6 7.3 3.8 7.3 0.8   2.6  0.5  1.8                  5  0.500                                                                             9.0  6.0  9.0 9.0 9.0 9.0 8.0 9.0 2.0   6.0  4.0  4.0                     0.250                                                                             9.0  5.0  9.0 9.0 9.0 9.0 5.0 8.0 4.0   5.0  4.0  5.0                     0.125                                                                             9.0  3.0  5.0 9.0 9.0 9.0 5.0 4.0 2.0   5.0  3.0  5.0                  6  0.500                                                                             9.0  4.0  7.0 9.0 9.0 9.0 7.0 9.0 3.0   5.0  3.0  2.0                     0.250                                                                             7.0  3.0  4.0 9.0 9.0 9.0 6.0 6.0 3.0   7.0  3.0  5.0                     0.125                                                                             9.0  0.0  5.0 9.0 7.0 9.0 4.0 4.0 4.0   5.0  2.0  2.0                  7  0.500                                                                             7.0  2.0  8.0 9.0 7.0 9.0 3.0 7.0 2.0   7.0  3.0  4.0                     0.250                                                                             4.0  0.0  6.0 8.0 7.0 8.0 2.0 6.0 4.0   6.0  3.0  5.0                     0.125                                                                             3.0  0.0  3.0 3.0 6.0 4.0 3.0 3.0 0.0   5.0  2.0  5.0                  8  0.500                                                                             9.0  9.0  3.0 9.0 9.0 --  0.0 9.0 2.0   2.0  3.0  2.0                     0.250                                                                             9.0  8.0  0.0 9.0 5.0 --  0.0 5.0 0.0   2.0  3.0  0.0                     0.125                                                                             9.0  7.0  0.0 9.0 4.0 --  0.0 0.0 0.0   3.0  3.0  0.0                  9  0.500                                                                             4.0  9.0  3.0 9.0 9.0 --  4.0 9.0 2.0   5.0  3.0  2.0                     0.250                                                                             0.0  8.0  0.0 9.0 3.0 --  0.0 8.0 0.0   5.0  2.0  0.0                     0.125                                                                             0.0  7.0  2.0 9.0 0.0 --  0.0 4.0 0.0   4.0  2.0  0.0                 10  0.500                                                                             0.0  0.0  0.0 9.0 2.0 --  0.0 0.0 0.0   2.0  0.0  0.0                     0.250                                                                             0.0  0.0  0.0 9.0 0.0 --  0.0 0.0 0.0   2.0  0.0  0.0                     0.125                                                                             0.0  0.0  0.0 9.0 0.0 --  0.0 0.0 0.0   2.0  0.0  0.0                 11  0.500                                                                             6.0  7.0  0.0 9.0 4.0 --  0.0 8.0 0.0   4.0  2.0  0.0                     0.250                                                                             0.0  9.0  0.0 9.0 0.0 --  0.0 0.0 0.0   3.0  0.0  0.0                     0.125                                                                             0.0  8.0  0.0 9.0 0.0 --  0.0 0.0 0.0   2.0  0.0  0.0                 12  0.500                                                                             0.0  0.0  9.0 0.0 0.0 --  0.0 0.0 0.0   0.0  0.0  0.0                     0.250                                                                             0.0  0.0  9.0 0.0 0.0 --  0.0 0.0 0.0   0.0  0.0  0.0                     0.125                                                                             0.0  0.0  4.0 0.0 0.0 --  0.0 0.0 0.0   0.0  0.0  0.0                 13  0.500                                                                             8.0  9.0  8.0 9.0 7.0 9.0 3.0 4.0 2.0   4.0  3.0  2.0                     0.250                                                                             8.0  7.0  7.0 8.0 7.0 7.0 2.0 2.0 0.0   3.0  2.0  1.0                     0.125                                                                             6.0  7.0  6.0 9.0 5.0 8.0 0.0 0.0 0.0   2.0  2.0  0.0                 14  0.500                                                                             9.0  4.0  0.0 9.0 0.0 3.0 0.0 0.0 0.0   1.0  0.0  0.0                     0.250                                                                             8.0  4.0  0.0 9.0 0.0 0.0 0.0 0.0 0.0   1.0  0.0  0.0                     0.125                                                                             6.0  0.0  0.0 9.0 0.0 0.0 0.0 0.0 0.0   1.0  1.0  0.0                 15  0.500                                                                             7.0  9.0  3.0 9.0 9.0 9.0 8.0 6.0 3.0   8.0  5.0  5.0                     0.250                                                                             5.0  9.0  2.0 9.0 6.0 8.0 7.0 4.0 3.0   7.0  5.0  3.0                     0.125                                                                             3.0  8.0  4.0 9.0 4.0 9.0 3.0 2.0 2.0   6.0  4.0  3.0                 16  0.500                                                                             6.0  9.0  5.0 9.0 7.0 9.0 6.0 6.0 4.0   7.0  6.0  3.0                     0.250                                                                             3.0  9.0  3.0 9.0 4.0 9.0 3.0 2.0 1.0   6.0  5.0  2.0                     0.125                                                                             0.0  8.0  2.0 9.0 0.0 9.0 0.0 0.0 0.0   5.0  5.0  1.0                 17  0.500                                                                             6.0  7.0  4.0 9.0 4.0 9.0 0.0 3.0 1.0   3.0  40   0.0                     0.250                                                                             3.0  9.0  2.0 9.0 0.0 9.0 0.0 0.0 0.0   2.0  2.0  0.0                     0.125                                                                             2.0  3.0  2.0 9.0 0.0 9.0 0.0 0.0 0.0   2.0  1.0  0.0                 21  0.500                                                                             --   --   7.0 --  --  9.0 --  --  --    --   --   --                  22  0.500                                                                             --   --   3.0 --  --  0.0 --  --  --    --   --   --                  24  0.500                                                                             --   --   0.0 --  --  0.0 --  --  --    --   --   --                  27  0.500                                                                             --   --   0.0 --  --  8.0 --  --  --    --   --   --                  28  0.500                                                                             4.0  7.0  3.0 7.0 6.0 6.0 3.0 3.0 --    4.0  1.0  1.0                     0.250                                                                             3.0  5.0  2.0 6.0 3.0 4.0 2.0 2.0 1.0   2.0  0.0  0.0                     0.125                                                                             0.0  5.0  0.0 3.0 2.0 3.0 0.0 0.0 0.0   1.0  0.0  0.0                 29  0.500                                                                             2.0  2.0  4.0 7.0 4.0 5.0 0.0 0.0 0.0   6.0  2.0  1.0                     0.250                                                                             0.0  4.0  2.0 5.0 4.0 3.0 0.0 0.0 0.0   5.0  1.0  1.0                     0.125                                                                             0.0  3.0  4.0 5.0 0.0 0.0 0.0 1.0 0.0   3.0  0.0  0.0                 30  0.500                                                                             3.0  9.0  5.0 9.0 5.0 6.0 5.0 7.0 1.0   6.0  0.0  1.0                     0.250                                                                             2.0  5.0  3.0 7.0 4.0 --  2.0 4.0 0.0   6.0  3.0  0.0                     0.125                                                                             0.0  2.0  0.0 4.0 2.0 5.0 0.0 0.0 0.0   5.0  1.0  0.0                 31  0.500                                                                             4.0  6.0  4.0 9.0 7.0 9.0 5.0 9.0 2.0   3.0  2.0  2.0                     0.250                                                                             4.0  --   --  9.0 8.0 3.0 7.0 7.0 2.0   3.0  2.0  2.0                     0.125                                                                             3.0  5.0  3.0 9.0 5.0 3.0 6.0 5.0 1.0   3.0  1.0  1.0                 32  0.500                                                                             2.0  4.0  2.0 3.0 3.0 6.0 2.0 2.0 0.0   2.0  1.0  0.0                     0.250                                                                             0.0  3.0  0.0 0.0 0.0 6.0 0.0 5.0 0.0   2.0  0.0  0.0                     0.125                                                                             0.0  3.0  0.0 0.0 0.0 0.0 0.0 4.0 0.0   2.0  0.0  0.0                 33  0.500                                                                             7.0  8.0  8.0 9.0 8.0 9.0 7.0 9.0 3.0   8.0  2.0  2.0                     0.250                                                                             7.0  7.0  6.0 9.0 8.0 4.0 5.0 7.0 2.0   7.0  1.0  2.0                     0.125                                                                             3.0  6.0  5.0 9.0 5.0 5.0 2.0 3.0 0.0   5.0  0.0  1.0                 34  0.500                                                                             0.0  0.0  0.0 0.0 0.0 8.0 0.0 0.0 0.0   0.0  0.0  0.0                     0.250                                                                             0.0  0.0  0.0 0.0 0.0 9.0 0.0 0.0 0.0   0.0  0.0  0.0                     0.125                                                                             0.0  0.0  0.0 0.0 0.0 0.0 0.0 0.0 0.0   0.0  0.0  0.0                 35  0.500                                                                             0.0  0.0  0.0 0.0 0.0 0.0 0.0 0.0 1.0   0.0  0.0  0.0                 36  0.500                                                                             0.0  0.0  4.0 9.0 0.0 0.0 0.0 0.0 0.0   0.0  0.0  0.0                     0.250                                                                             0.0  0.0  3.0 3.0 0.0 0.0 0.0 0.0 0.0   0.0  0.0  0.0                     0.125                                                                             0.0  0.0  0.0 0.0 0.0 0.0 0.0 0.0 0.0   0.0  0.0  0.0                 37  0.500                                                                             0.0  0.0  0.0 0.0 0.0 9.0 0.0 0.0 1.0   5.0  2.0  3.0                     0.250                                                                             0.0  0.0  0.0 9.0 0.0 9.0 0.0 0.0 0.0   5.0  0.0  2.0                     0.125                                                                             0.0  0.0  0.0 0.0 0.0 0.0 0.0 0.0 0.0   3.0  0.0  2.0                 38  0.500                                                                             0.0  0.0  0.0 0.0 0.0 0.0 0.0 0.0 1.0   3.0  1.0  2.0                 39  0.500                                                                             0.0  6.0  6.0 9.0 9.0 9.0 6.0 9.0 2.0   1.0  1.0  2.0                     0.250                                                                             3.0  6.5  5.5 9.0 5.0 9.0 5.0 8.5 2.0   5.0  0.5  2.0                     0.125                                                                             1.5  2.0  4.5 9.0 1.5 4.5 2.5 8.0 2.0   4.5  0.0  2.5                 40  0.250                                                                             0.0  0.0  1.0 7.5 0.5 4.5 3.0 3.5 2.5   2.0  0.0  0.5                     0.125                                                                             1.0  0.0  1.0 3.0 0.5 4.5 1.0 1.5 1.0   1.0  0.0  1.5                 41  0.500                                                                             0.0  0.0  0.0 9.0 6.0 9.0 0.0 8.0 2.0   5.0  0.0  2.0                     0.250                                                                             0.0  0.0  2.0 9.0 0.0 3.0 0.0 2.0 0.0   6.0  0.0  0.0                     0.125                                                                             0.0  0.0  2.0 9.0 5.0 0.0 0.0 0.0 0.0   5.0  0.0  0.0                 42  0.500                                                                             1.0  2.0  0.0 9.0 0.0 --  0.0 0.0 0.0   1.5  0.5  0.0                     0.250                                                                             0.0  0.0  0.0 9.0 0.0 --  0.0 2.0 0.0   1.0  0.5  0.0                     0.125                                                                             0.0  0.0  0.0 9.0 0.0 --  0.0 0.0 0.0   0.0  0.0  0.0                 43  0.500                                                                             3.0  3.0  4.5 9.0 3.5 --  8.5 9.0 1.0   3.5  0.5  2.0                     0.250                                                                             2.0  3.0  2.0 9.0 2.0 --  3.5 9.0 0.0   0.5  0.5  0.5                     0.125                                                                             3.0  5.5  1.0 9.0 0.0 --  0.0 4.0 0.5   1.5  0.5  1.0                 44  0.500                                                                             6.0  0.0  0.0 9.0 9.0 --  2.0 9.0 0.0   0.0  0.0  0.0                     0.250                                                                             0.0  0.0  --  9.0 9.0 --  0.0 8.0 0.0   0.0  0.0  0.0                     0.125                                                                             0.0  0.0  --  9.0 0.0 --  0.0 9.0 0.0   0.0  0.0  0.0                 45  0.500                                                                             9.0  0.0  0.0 9.0 0.0 --  7.0 9.0 1.0   3.0  1.0  0.0                     0.250                                                                             9.0  0.0  0.0 9.0 0.0 --  7.0 9.0 1.0   1.0  1.0  0.0                     0.125                                                                             0.0  0.0  0.0 9.0 0.0 --  0.0 0.0 0.0   0.0  0.0  0.0                 46  0.500                                                                             0.0  0.0  0.0 9.0 0.0 8.0 0.0 0.0 1.0   5.0  1.0  1.0                     0.250                                                                             0.0  0.0  0.0 7.0 0.0 7.0 0.0 0.0 1.0   7.0  1.0  3.0                     0.125                                                                             0.0  0.0  0.0 0.0 0.0 0.0 0.0 0.0 1.0   4.0  1.0  3.0                 __________________________________________________________________________

EXAMPLE 42 Rice Tolerance to Post-Transplant Applications andPreemergence Weed Control Under Flooded Paddy Conditions

The tolerance of transplanted rice to post-transplanted herbicideapplications is determined as follows: two ten-day-old rice seedlings(CV. Tebonnet) are transplanted into a silt loam soil in 32 oz. plasticcontainers with a diameter of 10.5 cm and no drainage holes. Aftertransplanting the containers are flooded and the water level ismaintained at 1.5 to 3 cm above the soil surface. Three days aftertransplanting, the flooded soil surface of the containers is treatedwith the selected aqueous/acetone 50/50 v/v mixture containing the testcompounds to provide the equivalent of about 0.5, 0.25, 0.125 and 0 063kg/ha of active ingredient. The treated containers are placed ongreenhouse benches, watered such that the water level is maintained asstated above, and cared for according to normal greenhouse procedures.Three to four weeks after treatment the test is terminated and eachcontainer is examined and herbicidal effect rated according to therating system provided in Example 40. The data obtained are reported inTable III-. The compounds evaluated are reported by compound numbergiven in Example 40.

Preemergence herbicidal activity under flooded paddy conditions isdetermined as follows: plant seeds or propagating organs are planted inthe top 0.5 cm of silt loam soil in 32 oz. plastic containers with adiameter of 10.5 cm and no drainage holes. Water is added to thesecontainers and maintained at 1.5 to 3 cm above the soil surface for theduration of the experiment. The test compounds are applied asaqueous/acetone mixtures 50/50 v/v pipetted directly into the floodwater to give the equivalent of about 0.5, 0.25, 0.125 and 0.063 kg/haof active ingredient. The treated containers are placed on greenhousebenches and cared for according to normal greenhouse procedures. Threeto four weeks after treatment the test is terminated and each containeris examined and herbicidal effect rated according to the rating systemprovided in Example 40. The data obtained are reported in Table III. Thecompounds evaluated are reported by compound number given in Example 40.

Plant species employed in this example are reported by headerabbreviation, common name and scientific name.

    ______________________________________                                        PLANT SPECIES EMPLOYED IN RICE TOLERANCE                                      /PREEMERGENCE WEED CONTROL EVALUATIONS                                        Header                                                                        Abb.    Common Name   Scientific Name                                         ______________________________________                                        ECHORC  Watergrass (Calif.)                                                                         ECHINOCHLOA ORYZOIDES                                                         (ARD.) FRITSCH                                          CYPIR   Rice Flatsedge                                                                              CYPERUS IRIA                                            CYPSE   Flatsedge     CYPERUS SEROTINUS,                                                            ROTTB.                                                  MOOVA   Monochoria    MONOCHORIA VAGINALIS,                                                         PRESL.                                                  SAGPY   Arrowhead (Pygmaea)                                                                         SAGITTARIA PYGMAEA, L.                                  ORYSAT  Rice, Tebonnet                                                                              ORYZA SATIVA, L.                                                              TEBONNET                                                ______________________________________                                    

                                      TABLE III                                   __________________________________________________________________________    PADDY CONDITIONS POST-TRANSPLANT RICE                                         PREEMERGENCE WEEDS                                                            Cpd.                                                                             Rate                                                                       No.                                                                              (kg/ha)                                                                            ECHORC                                                                             CYPIR                                                                             CYPSE                                                                              MOOVA                                                                              SAGPY                                                                              ORYSAT                                        __________________________________________________________________________     1 0.500                                                                              9.0  9.0 7.0  9.0  4.0  3.0                                              0.250                                                                              9.0  9.0 6.0  9.0  0.0  2.0                                              0.125                                                                              9.0  9.0 6.0  9.0  0.0  1.0                                            2 0.500                                                                              9.0  9.0 9.0  9.0  9.0  6.7                                              0.250                                                                              9.0  9.0 6.8  9.0  6.1  5.5                                              0.125                                                                              9.0  9.0 5.4  9.0  3.9  4.0                                              0.063                                                                              9.0  9.0 3.0  9.0  0.8  2.5                                            3 0.500                                                                              9.0  8.8 3.7  8.8  0.0  4.0                                              0.250                                                                              8.8  8.5 3.5  8.5  0.0  3.8                                              0.125                                                                              8.5  6.5 1.0  7.0  0.0  3.0                                              0.063                                                                              8.7  7.0 1.0  8.7  0.0  2.7                                            4 0.500                                                                              9.0  9.0 7.3  9.0  4.5  4.7                                              0.250                                                                              9.0  9.0 5.5  9.0  2.8  3.8                                              0.125                                                                              8.7  9.0 2.7  9.0  0.5  3.2                                              0.063                                                                              7.2  8.5 0.5  8.5  0.3  2.0                                            5 0.500                                                                              9.0  9.0 9.0  9.0  4.0  5.3                                              0.250                                                                              9.0  8.0 9.0  9.0  2.0  5.0                                              0.125                                                                              8.0  7.0 9.0  8.0  2.0  4.3                                              0.063                                                                              9.0  --  --   --   --   3.0                                            6 0.500                                                                              9.0  9.0 7.0  9.0  0.0  1.0                                              0.250                                                                              9.0  8.0 7.0  8.0  0.0  1.0                                              0.125                                                                              7.0  7.0 5.0  7.0  0.0  1.0                                            7 0.500                                                                              9.0  8.0 --   8.0  0.0  1.0                                              0.250                                                                              8.0  7.0 0.0  7.0  0.0  0.0                                              0.125                                                                              7.0  4.0 0.0  6.0  0.0  0.0                                            8 0.500                                                                              6.0  8.0 --   8.0  1.0  2.0                                              0.250                                                                              4.0  8.0 0.0  8.0  0.0  1.0                                              0.125                                                                              0.0  7.0 0.0  6.0  0.0  0.0                                              0.063                                                                              0.0  7.0 0.0  4.0  0.0  0.0                                            9 0.500                                                                              9.0  9.0 9.0  9.0  1.0  6.0                                              0.250                                                                              9.0  9.0 9.0  9.0  1.0  5.7                                              0.125                                                                              9.0  9.0 9.0  9.0  0.0  3.7                                              0.063                                                                              9.0  9.0 4.0  9.0  0.0  3.3                                           10 0.500                                                                              5.5  9.0 --   9.0  0.0  1.0                                              0.250                                                                              2.0  9.0 0.0  9.0  0.0  1.0                                              0.125                                                                              1.0  9.0 0.0  9.0  0.0  1.0                                              0.063                                                                              0.0  9.0 0.0  9.0  0.0  0.0                                           11 0.500                                                                              9.0  9.0 6.0  9.0  0.0  1.0                                              0.250                                                                              9.0  8.0 0.0  9.0  0.0  1.0                                              0.125                                                                              9.0  7.0 0.0  8.0  0.0  0.0                                              0.063                                                                              9.0  4.0 0.0  6.0  0.0  0.0                                           12 0.500                                                                              9.0  6.5 2.0  9.0  0.0  1.0                                              0.250                                                                              8.0  4.0 0.0  7.0  0.0  0.0                                              0.125                                                                              6.0  2.0 0.0  6.0  0.0  0.0                                              0.063                                                                              2.0  --  0.0  --   0.0  0.0                                           13 0.500                                                                              9.0  9.0 0.0  9.0  0.0  3.0                                              0.250                                                                              9.0  9.0 0.0  9.0  0.0  3.0                                              0.125                                                                              9.0  9.0 0.0  9.0  0.0  2.0                                              0.063                                                                              9.0  9.0 0.0  9.0  0.0  2.0                                           14 0.500                                                                              0.0  1.0 0.0  8.0  0.0  0.0                                              0.250                                                                              0.0  0.0 0.0  6.0  0.0  0.0                                              0.125                                                                              0.0  0.0 0.0  2.0  0.0  0.0                                              0.063                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           15 0.500                                                                              9.0  9.0 9.0  9.0  2.0  7.0                                              0.250                                                                              9.0  9.0 9.0  9.0  4.5  7.0                                              0.125                                                                              9.0  9.0 5.5  9.0  3.0  4.5                                              0.063                                                                              8.5  8.0 2.0  9.0  1.0  4.5                                           16 0.500                                                                              9.0  9.0 9.0  9.0  0.0  6.0                                              0.250                                                                              9.0  9.0 9.0  9.0  4.5  7.0                                              0.125                                                                              9.0  9.0 9.0  9.0  4.5  5.0                                              0.063                                                                              9.0  8.0 5.5  9.0  4.0  3.5                                           17 0.500                                                                              9.0  9.0 9.0  9.0  0.0  2.0                                              0.250                                                                              9.0  9.0 5.5  9.0  3.5  3.0                                              0.125                                                                              9.0  8.0 2.0  9.0  3.0  3.0                                           18 0.500                                                                              9.0  9.0 4.0  9.0  2.0  4.0                                              0.250                                                                              9.0  9.0 2.0  9.0  0.0  3.0                                              0.125                                                                              9.0  9.0 1.0  9.0  0.0  3.0                                              0.063                                                                              9.0  9.0 0.0  9.0  0.0  2.0                                              0.063                                                                              9.0  4.0 0.0  9.0  0.0  2.0                                           19 0.500                                                                              9.0  6.0 0.0  9.0  0.0  1.0                                              0.250                                                                              9.0  4.0 0.0  9.0  0.0  1.0                                              0.125                                                                              9.0  2.0 0.0  9.0  0.0  1.0                                              0.063                                                                              8.0  2.0 0.0  9.0  0.0  1.0                                           20 0.500                                                                              9.0  9.0 --   9.0  0.0  4.0                                              0.250                                                                              9.0  7.0 2.0  9.0  0.0  3.0                                              0.125                                                                              9.0  4.0 0.0  9.0  0.0  3.0                                              0.063                                                                              7.0  2.0 0.0  8.0  0.0  2.0                                           21 0.500                                                                              4.0  1.0 0.0  4.5  0.0  0.5                                              0.250                                                                              6.0  2.0 0.0  8.0  0.0  0.0                                              0.125                                                                              4.0  1.0 0.0  8.0  0.0  0.0                                              0.063                                                                              2.0  0.0 0.0  4.0  0.0  0.0                                           22 0.500                                                                              8.5  8.0 0.0  8.0  0.0  2.0                                              0.250                                                                              6.0  2.0 0.0  7.0  0.0  0.0                                              0.125                                                                              4.0  0.0 0.0  2.0  0.0  0.0                                              0.063                                                                              2.0  0.0 0.0  2.0  0.0  0.0                                           23 0.500                                                                              9.0  6.0 2.0  9.0  0.0  3.0                                              0.250                                                                              7.0  2.0 1.0  9.0  0.0  3.0                                              0.125                                                                              4.0  0.0 0.0  8.0  0.0  2.0                                              0.063                                                                              4.0  0.0 0.0  6.0  0.0  2.0                                           24 0.500                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           25 0.500                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           26 0.500                                                                              9.0  9.0 9.0  9.0  0.0  3.0                                              0.250                                                                              9.0  9.0 6.0  9.0  0.0  3.0                                              0.125                                                                              9.0  9.0 0.0  9.0  0.0  2.0                                              0.063                                                                              8.0  4.0 0.0  7.0  0.0  2.0                                           27 0.500                                                                              3.0  2.0 0.0  2.0  0.0  1.5                                              0.250                                                                              1.0  2.0 0.0  2.0  0.0  2.0                                              0.125                                                                              0.0  2.0 0.0  0.0  0.0  1.0                                              0.063                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           28 0.500                                                                              8.0  4.0 0.0  9.0  0.0  2.0                                              0.250                                                                              2.0  0.0 0.0  2.0  0.0  2.0                                              0.125                                                                              0.0  0.0 0.0  0.0  0.0  1.0                                              0.063                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           29 0.500                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           30 0.500                                                                              0.0  0.0 0.0  0.0  0.0  1.0                                           31 0.500                                                                              2.0  6.0 0.0  --   0.0  2.0                                              0.250                                                                              0.0  4.0 0.0  --   0.0  1.0                                              0.125                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                              0.063                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           32 0.500                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           33 0.500                                                                              9.0  9.0 0.0  9.0  0.0  4.0                                              0.250                                                                              9.0  9.0 0.0  9.0  0.0  3.0                                              0.125                                                                              9.0  9.0 0.0  9.0  0.0  3.0                                              0.063                                                                              8.0  9.0 0.0  9.0  0.0  3.0                                           34 0.500                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           35 0.500                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           36 0.500                                                                              4.0  1.0 0.0  1.0  0.0  0.0                                              0.250                                                                              4.0  0.0 0.0  0.0  0.0  0.0                                              0.125                                                                              2.0  0.0 0.0  0.0  0.0  0.0                                              0.063                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           37 0.500                                                                              2.0  0.0 0.0  1.0  0.0  2.0                                              0.250                                                                              0.0  0.0 0.0  1.0  0.0  1.0                                              0.125                                                                              0.0  0.0 0.0  0.0  0.0  1.0                                              0.063                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           38 0.500                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           39 0.500                                                                              9.0  9.0 8.0  9.0  3.0  5.3                                              0.250                                                                              9.0  9.0 5.0  9.0  1.0  5.0                                              0.125                                                                              8.8  9.0 7.0  9.0  0.0  3.5                                              0.063                                                                              8.0  9.0 1.0  9.0  0.0  2.5                                           40 0.500                                                                              9.0  8.0 0.0  9.0  0.0  1.5                                              0.250                                                                              5.5  6.5 0.0  8.5  0.0  1.5                                              0.125                                                                              3.0  5.0 0.0  5.5  0.0  0.5                                              0.063                                                                              1.5  3.5 0.0  4.5  0.0  0.5                                           41 0.500                                                                              9.0  9.0 1.0  9.0  0.0  0.0                                              0.250                                                                              9.0  8.0 0.0  9.0  0.0  0.0                                              0.125                                                                              4.0  6.0 0.0  9.0  0.0  0.0                                              0.063                                                                              1.0  0.0 0.0  8.0  0.0  0.0                                           42 0.500                                                                              0.0  2.0 0.0  0.0  0.0  2.0                                              0.250                                                                              0.0  0.0 0.0  0.0  0.0  1.0                                           43 0.500                                                                              9.0  9.0 2.0  9.0  2.0  4.0                                              0.250                                                                              9.0  9.0 0.0  9.0  0.0  4.0                                              0.125                                                                              9.0  9.0 0.0  9.0  0.0  3.0                                              0.063                                                                              9.0  6.0 0.0  8.0  0.0  2.0                                           44 0.500                                                                              9.0  9.0 9.0  9.0  2.0  3.0                                              0.250                                                                              9.0  9.0 1.0  9.0  1.0  2.0                                              0.125                                                                              9.0  9.0 0.0  8.0  0.0  1.0                                              0.063                                                                              7.0  7.0 0.0  6.0  0.0  1.0                                           45 0.500                                                                              9.0  9.0 9.0  9.0  9.0  6.0                                              0.250                                                                              8.0  9.0 9.0  6.0  2.0  4.0                                              0.125                                                                              8.0  9.0 9.0  6.0  0.0  2.0                                              0.063                                                                              5.0  8.0 0.0  2.0  0.0  2.0                                           46 0.500                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           __________________________________________________________________________

EXAMPLE 43 Preemergence Herbicidal Evaluation of Test Compounds in thePresence of Transplanted Rice under Flooded paddy Conditions

In this example, Deluvian paddy soil (Toyokawa paddy soil) is placed inplastic pots, 100 cm² ×9 cm in depth. Water is added to the level of thesoil surface in the pot and the mixture is paddled 3 cm in depth.

Pots are then variously sown with monocotyledenous weed seeds and tubersat 0-2 cm in soil depth, as well as transplanted rice plants at the 2.5leaf stage. The rice plants are transplanted at about 3 cm soil depth.Water is then added to all of the pots to 3 cm deep and kept at a depthof 3 cm for the duration of the test. Test compounds are applied in themanner described in Example 42 three days after transplanting the riceplants and sowing the weed seeds and tubers. The pots are then placed ongreenhouse benches and cared for in the conventional manner. Tests areexamined at 25 to 30 days after treatment and rated according to therating system provided in Example 40. The data obtained are recorded inTable IV below. The compounds evaluated are reported by compound numbergiven in Example 40.

    ______________________________________                                        PLANT SPECIES USED                                                            Abb.   Common Name   Scientific Name                                          ______________________________________                                        ECHCG  Barnyard Grass                                                                              ECHINOCHLOA CRUS-GALLI                                   SAGPY  Arrowhead (Pygmaea)                                                                         SAGITTARIA PYGMAEA                                       CYPSE  Flatsedge, perennial                                                                        CYPERUS SEROTINUS                                        MOOVA  Monochoria    MONOCHORIA VAGINALIS                                     CYPDI  Flatsedge, smallflower                                                                      CYPERUS DIFFORMIS                                        SCPJU  Bulrush, Japanese                                                                           SCIRPUS JUNCOIDES                                        ORYSAK Rice, Koshihikari                                                                           ORYZA SATIVA,                                                                 L. CV. KOSHIHIKARI                                       ______________________________________                                    

                  TABLE IV                                                        ______________________________________                                        PREEMERGENCE/POST-TRANSPLANT EVALUATION                                            Rate                                                                     Cpd. (kg/   ECH-   SAG- CYP- MOO-  CYP-                                       No.  ha)    CG     PY   SE   VA    DI   SCPJU ORYSAK                          ______________________________________                                        2    0.250  9.0    9.0  9.0  9.0   9.0  9.0   9.0                                  0.100  9.0    9.0  9.0  9.0   9.0  9.0   5.0                                  0.050  9.0    7.0  7.0  9.0   9.0  9.0   3.0                                  0.025  9.0    3.0  4.0  9.0   9.0  8.0   1.0                             3    0.250  9.0    3.0  9.0  9.0   9.0  9.0   8.0                                  0.100  9.0    1.0  8.0  7.0   9.0  9.0   5.0                                  0.050  9.0    0.0  5.0  5.0   8.0  7.0   1.0                                  0.025  8.0    0.0  0.0  3.0   5.0  5.0   0.0                             4    0.250  9.0    9.0  --   9.0   9.0  9.0   9.0                                  0.125  9.0    6.0  --   9.0   9.0  9.0   7.0                                  0.063  9.0    2.0  --   9.0   9.0  9.0   4.0                                  0.032  9.0    0.0  --   9.0   9.0  7.0   1.0                             5    0.250  9.0    8.0  --   9.0   9.0  9.0   2.0                                  0.125  8.0    9.0  --   9.0   9.0  9.0   2.0                                  0.063  8.0    3.0  --   9.0   9.0  6.0   0.0                                  0.032  8.0    1.0  --   9.0   8.0  4.0   0.0                             8    0.250  9.0    8.0  --   9.0   9.0  8.0   6.0                                  0.125  9.0    6.0  --   9.0   9.0  7.0   2.0                                  0.063  8.0    3.0  --   9.0   9.0  5.0   3.0                                  0.032  8.0    1.0  --   7.0   7.0  1.0   2.0                             9    0.250  9.0    9.0  --   9.0   9.0  9.0   9.0                                  0.125  9.0    9.0  --   9.0   9.0  9.0   9.0                                  0.063  9.0    9.0  --   6.0   9.0  9.0   9.0                                  0.032  9.0    2.0  --   6.0   9.0  6.0   6.0                             10   0.250  9.0    9.0  --   9.0   9.0  8.0   2.0                                  0.125  9.0    5.0  --   9.0   9.0  6.0   1.0                                  0.063  9.0    2.0  --   6.0   7.0  0.0   1.0                                  0.032  4.0    0.0  --   2.0   5.0  0.0   0.0                             ______________________________________                                    

EXAMPLE 44 Comparative Herbicidal Evaluations

The postemergence, preemergence and pre-weed/post-transplanted riceherbicidal properties of certain compounds of the present invention arecompared with certain 1,3,5-triazinone compounds described in U.S. Pat.No. 4,512,797. The evaluations are performed as described in Examples40, 41 and 42. The results are reported in Tables V, VI and VII. Data inTables V, VI and VII are reported by compound number given in Example 40for the compounds of the present invention or by comparative compoundletter for the compounds described in U.S. Pat. No. 4,512,797.

As can be seen from the data in Tables V-VII, the compounds of thepresent invention are more effective herbicidal agents, in general, thanthe compounds described in U.S. Pat. No. 4,512,797.

    ______________________________________                                         ##STR88##                                                                    Comparative Compound                                                          Letter              X.sub.4                                                                              Y.sub.1                                            ______________________________________                                        A                   F      Br                                                 B                   H      NO.sub.2                                           C                   F      F                                                  D                   F      NO.sub.2                                           E                   H      H                                                  F                   H      Cl                                                 ______________________________________                                    

                                      TABLE V                                     __________________________________________________________________________    Postemergence Comparative Evaluations                                         Com-                                                                              Rate                                                                      pound                                                                             (kg/ha)                                                                           ABUTH                                                                              AMBEL                                                                              CASOB                                                                             CHEAL                                                                             IPOSS                                                                             GALAP                                                                             ECHCG                                                                             SETVI                                                                             GLXMAW                                                                              ORYSAT                                                                             TRZAWO                                                                             ZEAMX               __________________________________________________________________________    2   0.500                                                                             9.0  8.0  9.0 8.5 9.0 9.0 9.0 9.0 8.3   7.5  8.5  8.3                     0.250                                                                             9.0  7.5  9.0 8.5 9.0 9.0 9.0 9.0 8.0   7.0  8.0  8.3                     0.125                                                                             9.0  7.3  9.0 8.7 8.7 9.0 6.7 9.0 7.2   6.3  7.5  8.4                     0.063                                                                             8.8  8.0  9.0 8.8 8.3 9.0 5.0 7.5 6.9   6.3  7.0  7.7                 A   0.500                                                                             9.9  5.0  --  9.0 9.0 --  2.0 5.0 5.0   --   --   20                      0.250                                                                             6.0  --   --  9.0 9.0 --  2.0 2.0 3.0   --   --   0.0                     0.125                                                                             6.0  2.0  --  9.0 7.0 --  0.0 2.0 3.0   --   --   0.0                     0.063                                                                             5.0  1.0  --  9.0 6.0 --  0.0 0.0 2.0   --   --   0.0                 3   0.250                                                                             8.9  9.0  8.4 7.4 8.9 8.4 7.9 7.9 6.3   6.6  7.6  6.9                     0.125                                                                             8.8  8.8  8.8 7.2 8.9 8.7 6.7 6.8 5.9   5.7  7.1  5.8                     0.063                                                                             8.1  8.6  8.4 6.0 8.3 8.3 5.1 5.1 5.3   5.1  6.8  4.8                     0.031                                                                             7.3  8.3  7.7 5.1 7.6 8.2 4.3 3.9 4.8   4.9  6.1  4.6                 B   0.250                                                                             9.0  7.0  5.5 4.5 9.0 4.5 3.5 2.0 4.3   5.0  4.3  4.3                     0.125                                                                             7.0  8.0  8.0 7.0 8.0 7.0 3.0 0.0 4.0   5.5  4.0  4.5                     0.063                                                                             7.0  4.5  4.0 2.5 9.0 2.5 2.0 1.0 4.0   4.5  3.0  3.3                     0.031                                                                             4.5  3.0  3.5 2.0 8.0 2.0 1.0 0.5 3.3   4.0  3.0  3.3                 4   0.250                                                                             9.0  8.9  8.4 9.0 9.0 8.1 8.9 9.0 7.3   6.4  8.2  8.9                     0.125                                                                             9.0  8.5  9.0 8.9 9.0 8.8 8.2 9.0 6.4   5.7  8.1  8.9                     0.063                                                                             8.9  8.0  8.4 8.8 8.9 8.4 6.0 8.6 5.7   5.0  7.3  8.7                     0.031                                                                             8.9  7.2  8.6 7.9 8.9 7.3 3.8 6.9 5.1   4.6  6.3  8.1                 C   0.250                                                                             7.0  6.0  6.0 7.0 9.0 7.0 2.0 1.0 5.0   3.5  4.5  4.5                     0.125                                                                             7.0  4.0  4.0 7.0 6.0 7.0 0.0 0.0 4.5   3.5  4.5  4.0                     0.063                                                                             4.0  3.0  4.0 4.0 5.0 6.0 0.0 0.0 4.5   3.5  4.0  3.5                     0.031                                                                             2.0  1.0  2.0 3.0 4.0 2.0 0.0 0.0 3.5   3.0  3.5  3.0                 16  0.125                                                                             9.0  9.0  9.0 6.5 9.0 9.0 3.7 1.3 5.6   5.8  8.4  4.2                     0.063                                                                             8.3  9.0  8.3 3.7 8.3 9.0 1.7 0.8 5.1   5.3  7.4  3.4                     0.031                                                                             8.0  9.0  9.0 3.0 7.0 8.0 0.7 0.0 4.6   5.3  6.4  3.0                     0.016                                                                             8.3  9.0  8.7 1.5 7.0 6.0 0.5 0.0 3.8   6.0  4.7  2.4                     0.008                                                                             5.5  7.0  5.5 0.0 6.0 4.5 0.0 0.0 3.3   4.0  4.5  2.0                 D   0.125                                                                             9.0  8.5  9.0 9.0 9.0 9.0 2.5 1.5 5.5   5.3  5.3  5.5                     0.063                                                                             9.0  8.0  6.0 7.0 7.3 8.5 2.0 1.3 4.7   4.8  5.3  4.2                     0.031                                                                             8.7  8.0  5.0 6.3 7.7 9.0 1.5 1.3 4.5   4.3  4.5  3.3                     0.016                                                                             8.3  7.3  4.3 7.3 7.3 8.0 3.0 1.0 4.2   3.8  3.5  3.3                     0.008                                                                             0.0  5.0  1.0 7.0 --  4.0 --  0.0 2.5   --   --   1.0                 28  0.500                                                                             9.0  7.0  6.5 9.0 9.0 4.5 2.0 4.0 5.0   3.0  2.0  4.5                     0.250                                                                             7.0  6.0  6.0 8.0 8.0 5.0 0.0 2.0 4.5   2.5  2.0  4.0                     0.125                                                                             6.0  4.0  5.0 6.0 6.0 4.0 0.0 1.0 3.5   2.0  2.0  2.5                     0.063                                                                             4.0  3.0  3.0 6.0 6.0 6.0 0.0 1.0 2.5   1.5  1.5  1.5                 E   0.500                                                                             6.0  5.0  2.0 8.0 6.0 2.5 3.0 2.0 3.5   3.0  1.5  2.5                     0.250                                                                             5.0  4.0  5.0 8.0 5.0 5.0 1.0 1.0 3.0   2.0  1.0  1.5                     0.125                                                                             5.0  2.0  3.0 7.0 5.0 4.0 0.0 0.0 2.5   2.0  1.0  1.5                     0.063                                                                             4.0  2.0  2.0 7.0 5.0 3.0 0.0 0.0 2.0   1.5  1.0  1.5                 39  0.500                                                                             9.0  9.0  9.0 9.0 9.0 9.0 8.0 9.0 7.0   4.5  5.5  8.5                     0.250                                                                             9.0  9.0  9.0 9.0 9.0 9.0 7.5 8.0 6.3   4.8  6.0  8.0                     0.125                                                                             9.0  8.5  9.0 9.0 9.0 8.0 4.5 4.5 5.5   4.3  4.8  6.5                     0.063                                                                             9.0  7.5  9.0 9.0 9.0 7.0 1.0 3.5 5.3   4.8  4.5  4.8                     0.032                                                                             8.5  6.5  9.0 8.0 7.0 8.5 3.0 4.5 4.5   3.3  3.8  4.3                     0.016                                                                             7.0  4.5  6.0 6.0 5.5 7.5 1.5 2.5 3.8   2.3  2.8  3.3                 F   0.500                                                                             9.0  7.0  6.5 9.0 7.0 6.0 2.0 3.0 5.5   3.0  3.5  4.0                     0.250                                                                             7.0  6.0  9.0 9.0 6.0 8.0 2.0 3.0 5.5   3.0  3.5  4.0                     0.125                                                                             5.0  6.0  8.0 8.0 5.0 6.0 1.0 2.0 4.0   3.0  3.0  3.0                     0.063                                                                             5.0  6.0  5.0 6.0 6.0 6.0 0.0 3.0 4.5   2.5  2.5  2.5                     0.032                                                                             4.0  3.0  4.0 5.0 4.0 6.0 0.0 1.0 3.5   1.5  1.5  2.0                     0.016                                                                             4.0  2.0  2.0 4.0 3.0 5.0 0.0 0.0 3.5   1.5  1.5  1.5                 __________________________________________________________________________

                                      TABLE VI                                    __________________________________________________________________________    Preemergence Comparative Evaluations                                          Com-                                                                              Rate                                                                      pound                                                                             (kg/ha)                                                                           ABUTH                                                                              AMBEL                                                                              CASOB                                                                             CHEAL                                                                             IPOSS                                                                             GALAP                                                                             ECHCG                                                                             SETVI                                                                             GLXMAW                                                                              ORYSAT                                                                             TRZAWO                                                                             ZEAMX               __________________________________________________________________________    2   0.500                                                                             9.0  8.5  9.0 9.0 9.0 9.0 8.5 9.0 8.5   8.0  5.0  6.5                     0.250                                                                             9.0  7.0  9.0 9.0 9.0 9.0 5.5 9.0 6.5   8.0  5.0  5.5                     0.125                                                                             6.0  3.7  9.0 9.0 8.0 9.0 5.0 8.3 3.7   4.5  4.0  4.0                     0.063                                                                             3.3  1.0  7.0 9.0 5.7 8.5 2.7 8.0 3.0   5.0  4.0  3.0                 A   0.500                                                                             5.0  6.0  --  9.0 8.0 --  7.0 8.0 2.0   --   --   1.0                     0.250                                                                             2.0  3.0  --  9.0 3.0 --  3.0 2.0 2.0   --   --   0.0                     0.125                                                                             1.0  2.0  --  9.0 2.0 --  2.0 1.0 0.0   --   --   0.0                     0.063                                                                             0.0  0.0  --  9.0 0.0 --  0.0 0.0 0.0   --   --   0.0                 3   0.250                                                                             3.8  8.7  7.2 9.0 6.1 8.5 4.6 7.8 3.5   6.1  2.3  2.8                     0.125                                                                             2.6  6.6  5.4 9.0 5.2 7.6 3.0 7.0 2.3   5.3  2.0  1.4                     0.063                                                                             1.4  5.4  4.0 9.0 4.3 7.2 2.8 6.4 0.8   4.8  1.2  0.8                     0.031                                                                             0.0  2.8  4.6 8.2 2.2 8.2 1.5 4.0 1.0   3.5  0.4  0.8                 B   0.250                                                                             9.0  3.5  9.0 4.5 9.0 9.0 3.5 0.5 1.0   6.0  4.0  2.5                     0.125                                                                             8.5  4.0  8.5 4.5 7.0 9.0 2.5 0.0 0.0   5.0  1.5  1.5                     0.063                                                                             4.5  0.0  6.5 4.5 6.0 4.5 1.5 0.0 0.0   3.0  0.0  0.0                     0.031                                                                             4.5  0.0  1.5 4.5 3.0 3.5 1.5 1.5 0.0   4.0  1.5  1.5                 4   0.250                                                                             8.2  5.8  6.6 9.0 7.3 9.0 5.7 8.7 2.2   2.9  1.7  2.7                     0.125                                                                             6.2  2.2  1.8 9.0 5.7 7.3 4.6 7.8 1.2   2.1  0.7  1.7                     0.063                                                                             3.7  0.7  0.8 9.0 3.3 3.7 3.1 6.5 0.7   1.7  0.7  1.0                     0.031                                                                             1.3  0.3  1.5 8.3 1.6 3.0 1.3 4.2 0.5   1.3  0.2  0.2                 C   0.250                                                                             4.0  0.0  2.0 9.0 3.0 9.0 4.0 2.0 0.0   2.0  2.0  0.0                     0.125                                                                             7.0  0.0  5.0 9.0 0.0 9.0 2.0 2.0 0.0   2.0  0.0  0.0                     0.063                                                                             2.0  0.0  3.0 7.0 2.0 8.0 0.0 4.0 0.0   0.0  0.0  0.0                     0.031                                                                             0.0  0.0  0.0 6.0 0.0 7.0 0.0 2.0 0.0   0.0  0.0  0.0                 16  0.250                                                                             3.0  9.0  3.0 9.0 4.0 9.0 3.0 2.0 1.0   6.0  5.0  2.0                     0.125                                                                             0.0  8.0  2.0 9.0 0.0 9.0 0.0 0.0 0.0   5.0  5.0  1.0                     0.063                                                                             0.0  6.0  0.0 9.0 0.0 9.0 0.0 0.0 0.0   3.0  3.0  0.0                     0.031                                                                             0.0  2.0  0.0 9.0 0.0 9.0 0.0 0.0 1.0   3.0  1.0  0.0                 D   0.250                                                                             9.0  9.0  5.0 9.0 5.0 9.0 4.0 3.0 1.0   7.0  2.0  0.0                     0.125                                                                             6.0  9.0  2.0 9.0 5.0 9.0 2.0 2.0 0.0   7.0  2.0  0.0                     0.063                                                                             6.0  7.0  3.0 9.0 3.0 8.0 0.0 0.0 0.0   7.0  2.0  0.0                     0.031                                                                             2.0  4.0  0.0 9.0 0.0 5.0 0.0 0.0 0.0   3.0  0.0  0.0                 28  1.000                                                                             7.0  5.0  3.0 9.0 7.0 5.0 6.0 6.0 0.0   4.0  1.0  1.0                     0.500                                                                             4.0  7.0  1.5 7.0 6.0 5.5 3.0 3.0 --    4.0  1.0  1.0                     0.250                                                                             3.0  5.0  2.0 6.0 3.0 4.0 2.0 2.0 1.0   2.0  0.0  0.0                     0.125                                                                             0.0  5.0  0.0 3.0 2.0 3.0 0.0 0.0 0.0   1.0  0.0  0.0                 E   1.000                                                                             4.0  3.0  0.0 5.0 3.0 7.0 4.0 3.0 2.0   7.0  1.0  1.0                     0.500                                                                             4.0  0.0  0.0 9.0 3.0 6.0 5.0 4.0 2.0   5.0  1.0  0.0                     0.250                                                                             3.0  0.0  0.0 7.0 4.0 5.0 2.0 3.0 0.0   5.0  1.0  0.0                     0.125                                                                             0.0  0.0  0.0 0.0 0.0 4.0 0.0 0.0 0.0   0.0  0.0  0.0                 39  0.500                                                                             0.0  6.0  6.0 9.0 9.0 9.0 6.0 9.0 2.0   1.0  1.0  2.0                     0.250                                                                             3.0  6.5  5.5 9.0 5.0 9.0 5.0 8.5 2.0   5.0  0.5  2.0                     0.125                                                                             1.5  2.0  4.5 9.0 1.5 4.5 2.5 8.0 2.0   4.5  0.0  2.5                     0.063                                                                             0.0  0.0  6.0 9.0 1.0 4.5 0.0 2.5 1.5   2.0  0.0  1.0                 F   0.500                                                                             4.0  4.0  1.0 9.0 5.0 2.0 2.0 2.0 1.0   6.0  1.0  1.0                     0.250                                                                             5.0  --   --  9.0 4.0 3.0 3.0 4.0 0.0   5.0  1.0  1.0                     0.125                                                                             3.0  --   0.0 9.0 8.0 0.0 3.0 3.0 0.0   5.0  0.0  0.0                     0.063                                                                             5.0  5.0  0.0 9.0 3.0 0.0 0.0 0.0 1.0   6.0  1.0  1.0                 __________________________________________________________________________

                                      TABLE VII                                   __________________________________________________________________________    Pre-Weed/Post-Transplanted Rice Comparative Evaluations                          Rate                                                                       Cpd.                                                                             (kg/ha)                                                                            ECHORC                                                                             CYPIR                                                                             CYPSE                                                                              MOOVA                                                                              SAGPY                                                                              ORYSAT                                        __________________________________________________________________________    3  0.250                                                                              8.8  8.5 3.5  8.5  0.0  3.8                                              0.125                                                                              8.5  6.5 1.0  7.0  0.0  3.0                                              0.063                                                                              8.7  7.0 1.0  8.7  0.0  2.7                                              0.031                                                                              7.5  3.0 0.0  7.0  0.0  1.0                                           B  0.250                                                                              8.0  8.0 3.0  8.0  4.0  4.5                                              0.125                                                                              6.5  7.0 3.0  6.5  3.0  2.5                                              0.063                                                                              4.0  7.0 0.0  9.0  2.0  3.0                                              0.031                                                                              0.0  0.0 0.0  9.0  2.0  2.0                                           4  0.250                                                                              9.0  9.0 4.8  9.0  2.6  3.7                                              0.125                                                                              8.8  9.0 2.0  9.0  0.4  3.6                                              0.063                                                                              7.4  8.6 0.4  8.6  0.2  2.1                                              0.031                                                                              6.0  7.4 0.0  8.4  0.0  1.6                                           C  0.250                                                                              2.0  8.0 0.0  9.0  0.0  5.0                                              0.125                                                                              0.0  8.0 0.0  9.0  0.0  3.0                                              0.063                                                                              0.0  6.0 0.0  9.0  0.0  1.0                                              0.031                                                                              0.0  4.0 0.0  9.0  0.0  1.0                                           16 0.250                                                                              9.0  9.0 9.0  9.0  4.5  7.0                                              0.125                                                                              9.0  9.0 9.0  9.0  4.5  5.0                                              0.063                                                                              9.0  8.0 5.5  9.0  4.0  3.5                                              0.031                                                                              9.0  7.5 4.5  9.0  3.5  3.0                                           D  0.250                                                                              9.0  9.0 4.0  9.0  9.0  6.0                                              0.125                                                                              9.0  9.0 --   9.0  9.0  3.0                                              0.063                                                                              9.0  9.0 0.0  7.0  7.0  3.0                                              0.031                                                                              9.0  7.0 0.0  4.0  4.0  3.0                                           28 1.000                                                                              7.0  7.0 0.0  9.0  0.0  3.0                                              0.500                                                                              8.5  6.5 0.0  9.0  0.0  2.0                                              0.250                                                                              2.0  0.0 0.0  2.0  0.0  2.0                                           E  1.000                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                              0.500                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                              0.250                                                                              0.0  0.0 0.0  0.0  0.0  0.0                                           39 0.250                                                                              9.0  9.0 5.0  9.0  1.0  5.0                                              0.125                                                                              8.8  9.0 7.0  9.0  0.0  3.5                                              0.063                                                                              8.0  9.0 1.0  9.0  0.0  2.5                                              0.031                                                                              7.8  9.0 0.0  9.0  0.0  1.8                                           F  0.250                                                                              0.0  4.0 0.0  8.0  0.0  2.0                                              0.125                                                                              0.0  2.0 0.0  8.0  0.0  1.0                                              0.063                                                                              0.0  2.0 0.0  6.0  0.0  0.0                                              0.031                                                                              0.0  0.0 0.0  4.0  0.0  0.0                                           __________________________________________________________________________

What is claimed is:
 1. A compound having the structural formula##STR89## wherein Ar is ##STR90## M is CX₄ or N; X, X₁, X₂, X₃, X₄ andY₁ are each independently hydrogen, halogen, nitro, cyano or C₁ -C₄haloalkyl;Y is hydrogen or halogen; R₁ is C₁ -C₄ alkyl; and R is C₃ -C₁₂alkylcarbonylalkyl, C₁ -C₁₂ haloalkylcarbonylalkyl, C₃ -C₁₂alkoxycarbonylalkyl or C₃ -C₁₂ haloalkoxycarbonylalkyl.